JPH0529039B2 - - Google Patents

Info

Publication number: JPH0529039B2
Authority: JP; Japan
Prior art keywords: compound; butyloxycarbonyl; ascamycin; formula; reaction
Prior art date: 1985-09-05
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

JP60196468A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6256500A (ja

Inventor

Kyoshi Isono

Makoto Ubukata

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

RIKEN Institute of Physical and Chemical Research

Original Assignee

RIKEN Institute of Physical and Chemical Research

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.)

1985-09-05

Filing date

1985-09-05

Publication date

1993-04-28

1985-09-05 Application filed by RIKEN Institute of Physical and Chemical Research filed Critical RIKEN Institute of Physical and Chemical Research

1985-09-05 Priority to JP60196468A priority Critical patent/JPS6256500A/ja

1987-03-12 Publication of JPS6256500A publication Critical patent/JPS6256500A/ja

1993-04-28 Publication of JPH0529039B2 publication Critical patent/JPH0529039B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 11
LZMCAAGVMFMSKC-UHFFFAOYSA-N Ascamycin Natural products OC1C(O)C(COS(=O)(=O)NC(=O)C(N)C)OC1N1C2=NC(Cl)=NC(N)=C2N=C1 LZMCAAGVMFMSKC-UHFFFAOYSA-N 0.000 claims description 9
LZMCAAGVMFMSKC-IZKXYQSCSA-N [(2r,3s,4r,5r)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl n-[(2s)-2-aminopropanoyl]sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)NC(=O)[C@@H](N)C)O[C@H]1N1C2=NC(Cl)=NC(N)=C2N=C1 LZMCAAGVMFMSKC-IZKXYQSCSA-N 0.000 claims description 9
-1 t-butyloxycarbonyl group Chemical group 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
238000001308 synthesis method Methods 0.000 claims 1
UVTLTEHAIUJFOX-ZETCQYMHSA-N tert-butyl 1-[(2s)-2-aminopropanoyl]imidazole-2-carboxylate Chemical compound C[C@H](N)C(=O)N1C=CN=C1C(=O)OC(C)(C)C UVTLTEHAIUJFOX-ZETCQYMHSA-N 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000000243 solution Substances 0.000 description 4
229930024421 Adenine Natural products 0.000 description 3
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
229960000643 adenine Drugs 0.000 description 3
229940126214 compound 3 Drugs 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
230000002194 synthesizing effect Effects 0.000 description 3
BIXYYZIIJIXVFW-UUOKFMHZSA-N (2R,3R,4S,5R)-2-(6-amino-2-chloro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BIXYYZIIJIXVFW-UUOKFMHZSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
OVGJPFXCBHGLNH-YFKPBYRVSA-N (2s)-2-[(2-methylpropan-2-yl)oxyamino]propanoic acid Chemical compound OC(=O)[C@H](C)NOC(C)(C)C OVGJPFXCBHGLNH-YFKPBYRVSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
108010052285 Membrane Proteins Proteins 0.000 description 1
APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
IHNHAHWGVLXCCI-FDYHWXHSSA-N [(2r,3r,4r,5s)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O IHNHAHWGVLXCCI-FDYHWXHSSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
244000000005 bacterial plant pathogen Species 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000001502 gel electrophoresis Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP60196468A 1985-09-05 1985-09-05 アスカマイシンの合成法 Granted JPS6256500A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP60196468A JPS6256500A (ja)	1985-09-05	1985-09-05	アスカマイシンの合成法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60196468A JPS6256500A (ja)	1985-09-05	1985-09-05	アスカマイシンの合成法

Publications (2)

Publication Number	Publication Date
JPS6256500A JPS6256500A (ja)	1987-03-12
JPH0529039B2 true JPH0529039B2 (de)	1993-04-28

Family

ID=16358302

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60196468A Granted JPS6256500A (ja)	1985-09-05	1985-09-05	アスカマイシンの合成法

Country Status (1)

Country	Link
JP (1)	JPS6256500A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5824657A (en) *	1997-03-18	1998-10-20	Cubist Pharmaceuticals, Inc.	Aminoacyl sulfamides for the treatment of hyperproliferative disorders

1985
- 1985-09-05 JP JP60196468A patent/JPS6256500A/ja active Granted

Also Published As

Publication number	Publication date
JPS6256500A (ja)	1987-03-12

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JPH0313239B2 (de)	1991-02-22
Castro-Pichel et al.	1987	A facile synthesis of ascamycin and related analogues
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