NO774233L - Fremgangsmaate for reduksjon av 2,5-diketoglukonsyre til 2-ketoglukonsyre og 2-ketogulonsyre - Google Patents

Fremgangsmaate for reduksjon av 2,5-diketoglukonsyre til 2-ketoglukonsyre og 2-ketogulonsyre

Info

Publication number: NO774233L
Authority: NO; Norway
Prior art keywords: acid; stated; diketogluconate; procedure; carbon atoms
Prior art date: 1976-12-10

Application number

NO774233A

Other languages

English (en)

Norwegian (no)

Inventor

Glenn Colton Andrews

Original Assignee

Pfizer

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-12-10

Filing date

1977-12-09

Publication date

1978-06-13

1977-10-20 Priority claimed from US05/843,946 external-priority patent/US4159990A/en

1977-12-09 Application filed by Pfizer filed Critical Pfizer

1978-06-13 Publication of NO774233L publication Critical patent/NO774233L/no

Links

239000002253 acid Substances 0.000 title claims description 50
VBUYCZFBVCCYFD-JJYYJPOSSA-N 2-dehydro-D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-JJYYJPOSSA-N 0.000 title claims description 43
238000000034 method Methods 0.000 title claims description 42
RXMWXENJQAINCC-DMTCNVIQSA-N 2,5-didehydro-D-gluconic acid Chemical compound OCC(=O)[C@@H](O)[C@H](O)C(=O)C(O)=O RXMWXENJQAINCC-DMTCNVIQSA-N 0.000 title claims description 24
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 72
239000000203 mixture Substances 0.000 claims description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
RKFLKNFLAJISPF-OGXRZFKVSA-L calcium;(3s,4s)-3,4,6-trihydroxy-2,5-dioxohexanoate Chemical compound [Ca+2].OCC(=O)[C@@H](O)[C@H](O)C(=O)C([O-])=O.OCC(=O)[C@@H](O)[C@H](O)C(=O)C([O-])=O RKFLKNFLAJISPF-OGXRZFKVSA-L 0.000 claims description 51
239000000243 solution Substances 0.000 claims description 31
235000010323 ascorbic acid Nutrition 0.000 claims description 27
239000011668 ascorbic acid Substances 0.000 claims description 27
229960005070 ascorbic acid Drugs 0.000 claims description 27
229910052783 alkali metal Inorganic materials 0.000 claims description 23
229910000033 sodium borohydride Inorganic materials 0.000 claims description 23
239000012279 sodium borohydride Substances 0.000 claims description 23
150000001340 alkali metals Chemical class 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 20
229910052708 sodium Inorganic materials 0.000 claims description 20
239000011734 sodium Substances 0.000 claims description 19
239000007858 starting material Substances 0.000 claims description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
125000005907 alkyl ester group Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
239000003456 ion exchange resin Substances 0.000 claims description 15
229920003303 ion-exchange polymer Polymers 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 13
-1 alkali metal cation Chemical class 0.000 claims description 13
239000007864 aqueous solution Substances 0.000 claims description 11
229910052791 calcium Inorganic materials 0.000 claims description 11
239000011575 calcium Substances 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 11
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
150000001241 acetals Chemical class 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 6
239000008139 complexing agent Substances 0.000 claims description 6
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
150000001342 alkaline earth metals Chemical class 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
239000006184 cosolvent Substances 0.000 claims description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 4
125000005207 tetraalkylammonium group Chemical group 0.000 claims description 4
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 3
238000007273 lactonization reaction Methods 0.000 claims description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 claims description 2
229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 2
239000011260 aqueous acid Substances 0.000 claims description 2
229940050410 gluconate Drugs 0.000 claims description 2
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
238000006722 reduction reaction Methods 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 16
235000010350 erythorbic acid Nutrition 0.000 description 16
229940026239 isoascorbic acid Drugs 0.000 description 16
229920005989 resin Polymers 0.000 description 16
239000011347 resin Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000004318 erythorbic acid Substances 0.000 description 15
239000000047 product Substances 0.000 description 15
238000001914 filtration Methods 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
229920001429 chelating resin Polymers 0.000 description 10
238000004811 liquid chromatography Methods 0.000 description 9
150000004702 methyl esters Chemical class 0.000 description 9
239000007787 solid Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000000855 fermentation Methods 0.000 description 7
230000004151 fermentation Effects 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
238000003756 stirring Methods 0.000 description 7
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
239000004327 boric acid Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
229920001467 poly(styrenesulfonates) Polymers 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
230000001105 regulatory effect Effects 0.000 description 5
PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 4
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
RGHNJXZEOKUKBD-SKNVOMKLSA-N L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SKNVOMKLSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229910052796 boron Inorganic materials 0.000 description 4
238000010531 catalytic reduction reaction Methods 0.000 description 4
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
230000000707 stereoselective effect Effects 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 description 3
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
159000000007 calcium salts Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
235000012208 gluconic acid Nutrition 0.000 description 3
229950006191 gluconic acid Drugs 0.000 description 3
239000005457 ice water Substances 0.000 description 3
ZPGGNADHMKRUDT-UHFFFAOYSA-N methyl 5-hydroxy-4-oxopyran-2-carboxylate Chemical compound COC(=O)C1=CC(=O)C(O)=CO1 ZPGGNADHMKRUDT-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
OFCZUBZXJNUXBT-UHFFFAOYSA-M sodium;3,4,5,6-tetrahydroxy-2-oxohexanoate Chemical compound [Na+].OCC(O)C(O)C(O)C(=O)C([O-])=O OFCZUBZXJNUXBT-UHFFFAOYSA-M 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229910014033 C-OH Inorganic materials 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229910014570 C—OH Inorganic materials 0.000 description 2
RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
PYMYPHUHKUWMLA-WISUUJSJSA-N aldehydo-L-xylose Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WISUUJSJSA-N 0.000 description 2
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229910052739 hydrogen Inorganic materials 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
KPHIBLNUVRGOGU-WDCZJNDASA-N methyl (3s,4r,5r)-3,4,5,6-tetrahydroxy-2-oxohexanoate Chemical compound COC(=O)C(=O)[C@@H](O)[C@H](O)[C@H](O)CO KPHIBLNUVRGOGU-WDCZJNDASA-N 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
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239000000126 substance Substances 0.000 description 2
150000005621 tetraalkylammonium salts Chemical class 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
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IZSRJDGCGRAUAR-MROZADKFSA-N 5-dehydro-D-gluconic acid Chemical compound OCC(=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O IZSRJDGCGRAUAR-MROZADKFSA-N 0.000 description 1
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238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
235000010378 sodium ascorbate Nutrition 0.000 description 1
229960005055 sodium ascorbate Drugs 0.000 description 1
235000010352 sodium erythorbate Nutrition 0.000 description 1
239000004320 sodium erythorbate Substances 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000011916 stereoselective reduction Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/62—Three oxygen atoms, e.g. ascorbic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/027—Keto-aldonic acids
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Saccharide Compounds (AREA)
Separation Of Suspended Particles By Flocculating Agents (AREA)
Seasonings (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

NO774233A 1976-12-10 1977-12-09 Fremgangsmaate for reduksjon av 2,5-diketoglukonsyre til 2-ketoglukonsyre og 2-ketogulonsyre NO774233L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US74950976A	1976-12-10	1976-12-10
US05/843,946 US4159990A (en)	1976-12-10	1977-10-20	Reduction of 2,5-diketogluconic acid

Publications (1)

Publication Number	Publication Date
NO774233L true NO774233L (no)	1978-06-13

Family

ID=27115134

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO774233A NO774233L (no)	1976-12-10	1977-12-09	Fremgangsmaate for reduksjon av 2,5-diketoglukonsyre til 2-ketoglukonsyre og 2-ketogulonsyre

Country Status (29)

Country	Link
JP (1)	JPS5384916A (xx)
AR (1)	AR218278A1 (xx)
AT (1)	AT354470B (xx)
AU (1)	AU498866B1 (xx)
BR (1)	BR7708220A (xx)
CA (1)	CA1110637A (xx)
CH (1)	CH629470A5 (xx)
CS (1)	CS208738B2 (xx)
DD (1)	DD135204A5 (xx)
DE (1)	DE2754719C3 (xx)
DK (1)	DK157139C (xx)
ES (1)	ES464780A1 (xx)
FI (1)	FI773722A (xx)
FR (1)	FR2373511A1 (xx)
GB (1)	GB1561324A (xx)
HU (1)	HU178688B (xx)
IE (1)	IE46106B1 (xx)
IT (1)	IT1192212B (xx)
LU (1)	LU78666A1 (xx)
MX (1)	MX4533E (xx)
NL (1)	NL170288C (xx)
NO (1)	NO774233L (xx)
NZ (1)	NZ185917A (xx)
PH (1)	PH13701A (xx)
PL (1)	PL114409B1 (xx)
PT (1)	PT67381B (xx)
SE (1)	SE7713979L (xx)
TR (1)	TR19706A (xx)
YU (1)	YU285077A (xx)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK154649C (da) *	1978-12-01	1989-05-08	Pfizer	Fremgangsmaade til fremstilling af 2-ketogulonsyre

1977
- 1977-11-28 MX MX776579U patent/MX4533E/es unknown
- 1977-11-29 PH PH20494A patent/PH13701A/en unknown
- 1977-12-02 NL NLAANVRAGE7713365,A patent/NL170288C/xx not_active IP Right Cessation
- 1977-12-03 YU YU02850/77A patent/YU285077A/xx unknown
- 1977-12-06 ES ES464780A patent/ES464780A1/es not_active Expired
- 1977-12-07 AR AR270273A patent/AR218278A1/es active
- 1977-12-07 CS CS778181A patent/CS208738B2/cs unknown
- 1977-12-08 AU AU31375/77A patent/AU498866B1/en not_active Expired
- 1977-12-08 DE DE2754719A patent/DE2754719C3/de not_active Expired
- 1977-12-08 SE SE7713979A patent/SE7713979L/xx not_active Application Discontinuation
- 1977-12-08 CA CA292,668A patent/CA1110637A/en not_active Expired
- 1977-12-09 FR FR7737189A patent/FR2373511A1/fr active Granted
- 1977-12-09 LU LU78666A patent/LU78666A1/xx unknown
- 1977-12-09 HU HU77PI607A patent/HU178688B/hu unknown
- 1977-12-09 FI FI773722A patent/FI773722A/fi not_active Application Discontinuation
- 1977-12-09 TR TR19706A patent/TR19706A/xx unknown
- 1977-12-09 CH CH1514877A patent/CH629470A5/fr not_active IP Right Cessation
- 1977-12-09 IT IT30544/77A patent/IT1192212B/it active
- 1977-12-09 AT AT882177A patent/AT354470B/de not_active IP Right Cessation
- 1977-12-09 NZ NZ185917A patent/NZ185917A/xx unknown
- 1977-12-09 JP JP14803377A patent/JPS5384916A/ja active Granted
- 1977-12-09 GB GB51415/77A patent/GB1561324A/en not_active Expired
- 1977-12-09 IE IE2503/77A patent/IE46106B1/en not_active IP Right Cessation
- 1977-12-09 DK DK549477A patent/DK157139C/da not_active IP Right Cessation
- 1977-12-09 PL PL1977202800A patent/PL114409B1/pl unknown
- 1977-12-09 NO NO774233A patent/NO774233L/no unknown
- 1977-12-09 PT PT67381A patent/PT67381B/pt unknown
- 1977-12-09 BR BR7708220A patent/BR7708220A/pt unknown
- 1977-12-12 DD DD77202532A patent/DD135204A5/xx unknown

Also Published As

Publication number	Publication date
DE2754719B2 (de)	1980-03-27
SE7713979L (sv)	1978-06-11
GB1561324A (en)	1980-02-20
IE46106B1 (en)	1983-02-23
TR19706A (tr)	1979-10-11
PH13701A (en)	1980-09-08
CA1110637A (en)	1981-10-13
ATA882177A (de)	1979-06-15
JPS569495B2 (xx)	1981-03-02
DD135204A5 (de)	1979-04-18
IT1192212B (it)	1988-03-31
AU498866B1 (en)	1979-03-29
NL170288B (nl)	1982-05-17
NL170288C (nl)	1982-10-18
FI773722A (fi)	1978-06-11
NL7713365A (nl)	1978-06-13
FR2373511A1 (fr)	1978-07-07
CS208738B2 (en)	1981-09-15
AT354470B (de)	1979-01-10
NZ185917A (en)	1980-03-05
PT67381B (en)	1979-05-18
YU285077A (en)	1982-08-31
DK549477A (da)	1978-06-11
CH629470A5 (en)	1982-04-30
DK157139C (da)	1990-04-16
AR218278A1 (es)	1980-05-30
JPS5384916A (en)	1978-07-26
HU178688B (en)	1982-06-28
DE2754719C3 (de)	1980-11-20
MX4533E (es)	1982-06-03
PT67381A (en)	1978-01-01
ES464780A1 (es)	1979-06-01
IE46106L (en)	1978-06-10
PL202800A1 (pl)	1978-08-28
PL114409B1 (en)	1981-01-31
LU78666A1 (fr)	1979-06-13
DE2754719A1 (de)	1978-06-15
BR7708220A (pt)	1978-08-15
DK157139B (da)	1989-11-13
FR2373511B1 (xx)	1980-06-06

Publication	Publication Date	Title
TANAKA et al.	1986	Tannins and related compounds. XLI.: Isolation and characterization of novel ellagitannins, punicacorteins A, B, C, and D, and punigluconin from the bark of Punica granatum L.
US7692041B2 (en)	2010-04-06	Method of oxidation using nitric acid
Anet	1959	Chemistry of Non-enzymic Browning. VII. Crystalline Di-D-fructose-glycine and some related compounds
Danishefsky et al.	1986	The total synthesis of (.+-.)-N-acetylneuraminic acid (NANA). A remarkable hydroxylation of a (Z)-enoate
US3975372A (en)	1976-08-17	Preparation of 12,13-desepoxy-12,13-dehydrorosamicin
Mackie et al.	1965	1, 2-O-ISOPROPYLIDENE-α-d-GLUCOFURANOSE-5-d AND-5, 6, 6′-d 3
US4108891A (en)	1978-08-22	Process for oxidation of monosaccharides
Dick et al.	1965	Synthesis of 4-Acetamido-4-deoxy-sugars
US4159990A (en)	1979-07-03	Reduction of 2,5-diketogluconic acid
MORGENLIE	1975	Oxidation of Carbohydrate Derivatives with Silver Carbonate on Celite. X. Identification of Three Mono-O-isopropylidene
US4294766A (en)	1981-10-13	Preparation of pure potassium ribonate and ribonolactone
Pravdic et al.	1967	Behavior of 2-acetamido-2-deoxy-D-mannose with isopropenyl acetate in the presence of p-toluenesulfonic acid. I. Isolation and identification of derivatives of 2-amino-D-glucal (2-amino-1, 2-dideoxy-D-arabino-hex-1-enopyranose) and of other products
NO774233L (no)	1978-06-13	Fremgangsmaate for reduksjon av 2,5-diketoglukonsyre til 2-ketoglukonsyre og 2-ketogulonsyre
US2153311A (en)	1939-04-04	Process for preparing 2-keto-aldonic acids and their salts
US4230880A (en)	1980-10-28	2,5-Diketogluconic acid esters
US3954809A (en)	1976-05-04	Preparation of l-ascorbate 2-sulfate from l-ascorbic acid
Baer et al.	1985	The formation of branched-chain deoxypentofuranosides by ring contraction in the reductive desulfonyloxylation of hexopyranoside p-toluenesulfonates
US4337350A (en)	1982-06-29	Reduction of 2,5-diketogluconic acid
Kuzuhara et al.	1975	Stereoselective synthesis of 5-O-carbamoylpolyoxamic acid (2-amino-5-O-carbamoyl-2-deoxy-l-xylonic acid
Gachon et al.	1975	GRISORIXIN, AN IONOPHOROUS ANTIBIOTIC OF THE NIGERICIN GROUP II. CHEMICAL AND STRUCTURAL STUDY OF GRISORIXIN AND SOME DERIVATIVES
KR860001121A (ko)	1986-02-22	신규 프리마이신 염의 제조방법
Nakagawa et al.	1987	Denitration of carbohydrate α-nitroepoxides by nucleophiles
US3721663A (en)	1973-03-20	Novel method for preparing ascorbic acid compounds and novel intermediates for preparing same
GB2030145A (en)	1980-04-02	Asorbic or erythorbic acid process
Hricoviniova et al.	1998	Molybdic Acid-Catalyzed Mutual Interconversions of 2-C-(Hydroxymethyl)-D-glucose with D-manno-Hept-2-ulose and 2-C-(Hydroxymethyl)-D-mannose with Dg/uco-Hept-2-ulose