A DIASTEREOSELECTIVE SYNTHESIS OF (S,S)-ALPHA-FLUORO-2,2-DIMETHYL-1,3-DIOXOLANE-4-PROPANOIC ACID METHYL-ESTER, A KEY INTERMEDIATE FOR THE PREPARATION OF ANTI-HIV EFFECTIVE FLUORODIDEOXYNUCLEOSIDES

被引：31

作者：

SIDDIQUI, MA ^{[1
]}

MARQUEZ, VE ^{[1
]}

DRISCOLL, JS ^{[1
]}

BARCHI, JJ ^{[1
]}

机构：

[1] NCI,DIV CANC TREATMENT,MED CHEM LAB,DEV THERAPEUT PROGRAM,BETHESDA,MD 20892

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(00)76880-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S,S)-alpha-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester (10), a key intermediate for the preparation of anti-HIV active 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl) adenine (1, FddA) and 1-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)cytosine (2, FddC) was prepared via the diastereoselective fluorination of the chiral imide enolate obtained from 8 with N-fluorobenzenesulfonimide. The overall yield of 10 from the readily available 1,2:5,6-di-O-isopropylidene-D-mannitol was 25% (de 93%).

引用

页码：3263 / 3266

页数：4

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