A HIGHLY STEREOSELECTIVE SYNTHESIS OF ANTI-HIV 2',3'-DIDEOXYNUCLEOSIDES AND 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES

被引：80

作者：

BEACH, JW ^{[1
]}

KIM, HO ^{[1
]}

JEONG, LS ^{[1
]}

NAMPALLI, S ^{[1
]}

ISLAM, Q ^{[1
]}

AHN, SK ^{[1
]}

BABU, JR ^{[1
]}

CHU, CK ^{[1
]}

机构：

[1] UNIV GEORGIA,COLL PHARM,DEPT MED CHEM,ATHENS,GA 30602

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 14期

关键词：

D O I：

10.1021/jo00040a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general total synthetic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented. Introduction of an alpha-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give greater-than-or-equal-to 95% beta-isomer. This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine. The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.

引用

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页码：3887 / 3894

页数：8

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