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Process for the diastereoselective synthesis of nucleoside analogues

A selective, enantiomeric technique, applied in organic chemistry and other directions, which can solve the problems of expensive, highly reactive, unstable compounds, etc.

Inactive Publication Date: 2004-06-02
GLAXO GROUP LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In particular, they are highly reactive and unstable compounds, thus, they are dangerous to use
Furthermore, they are expensive and have significant toxic effects

Method used

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  • Process for the diastereoselective synthesis of nucleoside analogues
  • Process for the diastereoselective synthesis of nucleoside analogues
  • Process for the diastereoselective synthesis of nucleoside analogues

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] 4-amino-1-(2R-hydroxymethyl-[1,3]oxathiolane-5S-yl)- 1H-pyrimidin-2-one

[0109] (a) (2R,5R)-5-Hydroxy-[1,3]oxathiolane-2-carboxylic acid, 2S -Isopropyl-5R-methyl-1R-cyclohexyl ester

[0110] A mixture of l-menthylglyoxylate hydrate (25g) and acetic acid (2.5ml) in toluene (125ml) was stirred and heated at reflux. Water was removed by azeotropic distillation over a Dean-Stark trap. The resulting l-menthyl glyoxylate solution was concentrated by distillation under reduced pressure, and about 70 ml of distillate was collected, followed by cooling to 20-25°C. The volume was adjusted to 75ml by adding about 15ml of toluene, dithianediol (8.25g) was added and the mixture was heated at reflux for about 1 hour. The mixture was cooled to about 80°C and cleared. The filtrate was cooled to 0-5°C, a solution of triethylamine (1.5ml) in hexane (150ml) was added at 0-5°C in about 1.25 hours, and the resulting suspension was stirred at 0-5°C for 6 hours , and then, the pr...

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Abstract

A diastereoselective process for the preparation of compounds of formula (I), wherein W is S, S=O, SO2, or O; X is S, S=O, SO2, or O; R1 is hydrogen or acyl, and R2 is a purine or pyrimidine base or an analogue or derivative thereof, is described.

Description

Technical field: [0001] This application is a divisional application of Chinese patent application 95193466.X (invention title "Diastereoselective synthesis method of nucleoside analogs") submitted on April 21, 1995. The present invention relates to a diastereoselective method for the preparation of optically active cis nucleoside analogs and derivatives. Background technique: [0002] Nucleosides and their analogs and derivatives are an important class of therapeutic agents. For example, many nucleoside analogs show antiviral activity against retroviruses such as human immunodeficiency virus (HIV), hepatitis B virus (HBV), and human T-lymphotropic virus (HTLV) (PCT Publication WO89 / 05662 and European Patent publication 0349242A2). [0003] In particular, 4-amino-1-(2R-hydroxymethyl-[1,3]oxathiolane-5S disclosed in International Application PCT / GB91 / 00706, Publication No. WO91 / 17159 can be represented by -yl)-1H-pyrimidin-2-one: [0004] [0005] (Also known as 3TC T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07DC07D327/04C07D339/06C07D411/04C07D473/00C07D473/18C07D473/34
CPCC07D473/00C07D411/04C07D327/04
Inventor M·D·古伊尔P·O·德莱耶M·L·希尔A·J·怀黑德R·科恩比P·哈列特
Owner GLAXO GROUP LTD
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