Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]-guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]2-amino-9H-purine (famciclovir)

被引：23

作者：

Brand, B ^{[1
]}

Reese, CB ^{[1
]}

Song, Q ^{[1
]}

Visintin, C ^{[1
]}

机构：

[1] Kings Coll London, Dept Chem, London WC2R 2LS, England

来源：

TETRAHEDRON | 1999年 / 55卷 / 16期

关键词：

antivirals; purines; alkylation; regioselection;

D O I：

10.1016/S0040-4020(99)00169-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Guanine 11 was converted, in a one pot reaction, into 2-amino-6-[(4-chlorophenyl)sulfanyl]purine 9a in 88% isolated yield. 4-Acetoxy-3-(acetoxymethyl)butanol 23 was prepared from 2-chloroethanol in five steps and in 46% overall yield. The mesylate ester of compound 23 reacted with 9a in the presence of potassium carbonate with a high degree of regioselectivity (89%) to give the N-9 alkylated product 26 which was isolated in 80% yield. Acidic hydrolysis of the latter compound 26 gave penciclovir 4 in virtually quantitative yield. Penciclovir 4 and famciclovir 5 were prepared from 2-amino-6-[(4-chlorophenyl)sulfanyl]puri 9a in four and five steps, respectively, by procedures involving initial alkylation with 1,2-dibromoethane. The overall yields obtained were 65 and ca. 60%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5239 / 5252

页数：14

共 26 条

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