JPS643196A - Production of 2',3'-dideoxycytidine - Google Patents
Production of 2',3'-dideoxycytidineInfo
- Publication number
- JPS643196A JPS643196A JP15454087A JP15454087A JPS643196A JP S643196 A JPS643196 A JP S643196A JP 15454087 A JP15454087 A JP 15454087A JP 15454087 A JP15454087 A JP 15454087A JP S643196 A JPS643196 A JP S643196A
- Authority
- JP
- Japan
- Prior art keywords
- expressed
- formula
- compound
- bromo
- dideoxycytidine
- Prior art date
- 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.)
- Granted
Links
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- 208000030507 AIDS Diseases 0.000 abstract 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 abstract 2
- 239000002994 raw material Substances 0.000 abstract 2
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 abstract 1
- RVZZYKULNCMTCR-FDDSLVSWSA-N 4-amino-1-[(2R,3S,4S,5R)-3-bromo-4-hydroxy-5-(hydroxymethyl)-4-methylsulfonyloxolan-2-yl]pyrimidin-2-one Chemical compound S(=O)(=O)(C)[C@@]1([C@H]([C@@H](O[C@@H]1CO)N1C(=O)N=C(N)C=C1)Br)O RVZZYKULNCMTCR-FDDSLVSWSA-N 0.000 abstract 1
- CIOFRDQJQVPSOE-YLWLKBPMSA-N 4-amino-1-[(2r,5s)-3-bromo-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1C(Br)=C[C@@H](CO)O1 CIOFRDQJQVPSOE-YLWLKBPMSA-N 0.000 abstract 1
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 abstract 1
- BRLGFSRIVNCSDB-AAQQEJRNSA-N [(2R,3R,4S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)-4-methylsulfonyloxolan-3-yl] methanesulfonate Chemical compound S(=O)(=O)(C)[C@@]1([C@@H](O[C@@H]([C@H]1OS(=O)(=O)C)CO)N1C(=O)N=C(N)C=C1)O BRLGFSRIVNCSDB-AAQQEJRNSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229960000523 zalcitabine Drugs 0.000 abstract 1
Landscapes
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
PURPOSE: To obtain the titled compound useful as a remedy for AIDS (acquired immunodeficiency syndrome) in high yield at a low cost using readily available raw materials, by debrominating and hydrogenating bromo-didehydro- dideoxycytidine.
CONSTITUTION: 2'-Bromo-2',3'-didehydro-2',3'-dideoxycytidine expressed by formula I is debrominated and hydrogenated to afford the aimed compound expressed by formula II. Furthermore, the compound expressed by formula I which is a starting raw material is a novel substance and can be produced by, e.g. mesylating an N,O5'-diacylcytidine, prepared by mesylating cytidine and expressed by formula III to provide an N,O5'-diacyl-O2',O3'-dimesylcytidine expressed by formula IV, reacting the resultant compound with lithium bromide in a nonaqueous solvent to afford an N,O5'-diacyl-O3'-mesyl-2'-bromo-2'-deoxycytidine expressed by formula V and reacting the obtained compound with an alkali metal alcoholate.
COPYRIGHT: (C)1989,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15454087A JPH0692394B2 (en) | 1987-06-23 | 1987-06-23 | Method for producing 2 ', 3'-dideoxycytidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15454087A JPH0692394B2 (en) | 1987-06-23 | 1987-06-23 | Method for producing 2 ', 3'-dideoxycytidine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH013196A JPH013196A (en) | 1989-01-06 |
| JPS643196A true JPS643196A (en) | 1989-01-06 |
| JPH0692394B2 JPH0692394B2 (en) | 1994-11-16 |
Family
ID=15586492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15454087A Expired - Lifetime JPH0692394B2 (en) | 1987-06-23 | 1987-06-23 | Method for producing 2 ', 3'-dideoxycytidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0692394B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1297565C (en) * | 2004-03-15 | 2007-01-31 | 陆锦康 | Method for preparing 2',3'2-dideoxycytidine |
-
1987
- 1987-06-23 JP JP15454087A patent/JPH0692394B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1297565C (en) * | 2004-03-15 | 2007-01-31 | 陆锦康 | Method for preparing 2',3'2-dideoxycytidine |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0692394B2 (en) | 1994-11-16 |
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