JPS637200B2 - - Google Patents

Info

Publication number: JPS637200B2
Authority: JP; Japan
Prior art keywords: group; reaction; deoxyguanosine; formula; allenesulfonyl
Prior art date: 1979-12-03
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

Application number

JP54155624A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5679700A (en

Inventor

Shinji Sakata

Tooru Ueda

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.)

Yamasa Shoyu KK

Original Assignee

Yamasa Shoyu KK

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.)

1979-12-03

Filing date

1979-12-03

Publication date

1988-02-15

1979-12-03 Application filed by Yamasa Shoyu KK filed Critical Yamasa Shoyu KK

1979-12-03 Priority to JP15562479A priority Critical patent/JPS5679700A/ja

1981-06-30 Publication of JPS5679700A publication Critical patent/JPS5679700A/ja

1988-02-15 Publication of JPS637200B2 publication Critical patent/JPS637200B2/ja

Status Granted legal-status Critical Current

Links

-1 alkylsulfonyl halide Chemical class 0.000 claims description 11
YKBGVTZYEHREMT-KVQBGUIXSA-N 2'-deoxyguanosine Chemical class C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 YKBGVTZYEHREMT-KVQBGUIXSA-N 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
YKBGVTZYEHREMT-UHFFFAOYSA-N 2'-deoxyguanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1CC(O)C(CO)O1 YKBGVTZYEHREMT-UHFFFAOYSA-N 0.000 claims description 2
VGONTNSXDCQUGY-UHFFFAOYSA-N desoxyinosine Natural products C1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 VGONTNSXDCQUGY-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
229910000037 hydrogen sulfide Inorganic materials 0.000 description 5
239000000203 mixture Substances 0.000 description 5
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
238000000862 absorption spectrum Methods 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000007810 chemical reaction solvent Substances 0.000 description 4
SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
238000000034 method Methods 0.000 description 2
IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
229910052979 sodium sulfide Inorganic materials 0.000 description 2
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
JAPYIBBSTJFDAK-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)benzenesulfonyl chloride Chemical compound CC(C)C1=CC(C(C)C)=C(S(Cl)(=O)=O)C(C(C)C)=C1 JAPYIBBSTJFDAK-UHFFFAOYSA-N 0.000 description 1
PVJZBZSCGJAWNG-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C(C)=C1 PVJZBZSCGJAWNG-UHFFFAOYSA-N 0.000 description 1
OTDJAMXESTUWLO-UUOKFMHZSA-N 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-oxolanyl]-3H-purine-6-thione Chemical compound C12=NC(N)=NC(S)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OTDJAMXESTUWLO-UUOKFMHZSA-N 0.000 description 1
KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012264 purified product Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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)

JP15562479A 1979-12-03 1979-12-03 2'-deoxyguanosine derivative and its preparation Granted JPS5679700A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP15562479A JPS5679700A (en)	1979-12-03	1979-12-03	2'-deoxyguanosine derivative and its preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP15562479A JPS5679700A (en)	1979-12-03	1979-12-03	2'-deoxyguanosine derivative and its preparation

Publications (2)

Publication Number	Publication Date
JPS5679700A JPS5679700A (en)	1981-06-30
JPS637200B2 true JPS637200B2 (fi)	1988-02-15

Family

ID=15610064

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP15562479A Granted JPS5679700A (en)	1979-12-03	1979-12-03	2'-deoxyguanosine derivative and its preparation

Country Status (1)

Country	Link
JP (1)	JPS5679700A (fi)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0369355A (ja) *	1989-08-10	1991-03-25	Jiyanisu Kogyo Kk	セラミック化粧パネルの中間層を形成するシート状材料およびその製造法

1979
- 1979-12-03 JP JP15562479A patent/JPS5679700A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0369355A (ja) *	1989-08-10	1991-03-25	Jiyanisu Kogyo Kk	セラミック化粧パネルの中間層を形成するシート状材料およびその製造法

Also Published As

Publication number	Publication date
JPS5679700A (en)	1981-06-30

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JP2004513131A (ja)	2004-04-30	相間移動触媒を用いたインドロカルバゾールのグリコシド化
JPH0859662A (ja)	1996-03-05	Ｎ−９置換グアニン化合物の調製
JPS637200B2 (fi)	1988-02-15
JP2678758B2 (ja)	1997-11-17	新規なプロパン誘導体
JPH10130244A (ja)	1998-05-19	アシクロヌクレオシドの製造方法
JPH061776A (ja)	1994-01-11	置換ピラジンカルボニトリルの製造方法
JPS5828279B2 (ja)	1983-06-15	ウリジンユウドウタイノセイゾウホウ
JPH013194A (ja)	1989-01-06	２′−ブロモ−２′，３′−ジデヒドロ−２′，３′−ジデオキシシチジン及びその製造法
HU198949B (en)	1989-12-28	Process for producing 5-substituted-3'azido-2',3'-dideoxyribonucleosides
BRPI0619928A2 (pt)	2011-10-25	processo de produção de 2', 2'-difluornucleosìdeo e intermediário
JPH0154359B2 (fi)	1989-11-17
JPH10168068A (ja)	1998-06-23	アシクロヌクレオシドの製造方法
JPS6139957B2 (fi)	1986-09-06
US3898142A (en)	1975-08-05	Photolytic cyclization of an amino-keto acylate
JP2547125B2 (ja)	1996-10-23	２’，３’−ジデオキシ−２’，３’−ジ置換−ヌクレオシド類とその製造方法
JP4055246B2 (ja)	2008-03-05	５−クロロ−６−（α−フルオロアルキル）−４−ピリミドン及びその製法
JPS6140669B2 (fi)	1986-09-10
JPS5982396A (ja)	1984-05-12	５―置換ウラシルヌクレオシドの製造法
JP2001011038A (ja)	2001-01-16	二級アルキル鎖を有する新規イソシアネートおよびセミカルバジド並びにその合成法
JPH01226862A (ja)	1989-09-11	Ｎ，ｎ−ジアルキルヒドラジン類の製造方法
JPH0529237B2 (fi)	1993-04-28
JPS6358833B2 (fi)	1988-11-17
JPH06192285A (ja)	1994-07-12	１−（β−Ｄ−エリスロ−ペントフラン−２−ウロシル）ピリミジン誘導体の製造法
JPH0428277B2 (fi)	1992-05-13
JPH03264582A (ja)	1991-11-25	２’，３’―ジデオキシ―２’，３’―ジ置換―ヌクレオシド類とその製造方法

JPS637200B2 - - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=15610064

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

Also Published As

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