Electrophilic addition to 4-thio furanoid glycal:: a highly stereoselective entry to 2′-deoxy-4′-thio pyrimidine nucleosides

被引：33

作者：

Haraguchi, K ^{[1
]}

Nishikawa, A ^{[1
]}

Sasakura, E ^{[1
]}

Tanaka, H ^{[1
]}

Nakamura, K ^{[1
]}

Miyasaka, T ^{[1
]}

机构：

[1] Showa Univ, Sch Pharmaceut Sci, Shinagawa Ku, Tokyo 1428555, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 22期

关键词：

thiosugars; glycals; nucleosides; addition reactions;

D O I：

10.1016/S0040-4039(98)00543-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Thio furanoid glycals with different types of O-silyl protection have been prepared from benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside. Face-selectivity for PhSeCl- or N-iodosuccimide-initiated addition of a pyrimidine base to the thioglycal was found to be controlled by O-silyl protecting groups. Using the thioglycal protected with a 3,5-O-di-t-butylsilyl group, a highly stereoselective synthesis of beta-2'-deoxy-4'-thio pyrimidine nucleosides has been accomplished. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3713 / 3716

页数：4

共 23 条

[21] NUCLEOSIDE SYNTHESES .23. ON THE MECHANISM OF NUCLEOSIDE SYNTHESIS [J].

VORBRUGGEN, H ;

HOFLE, G .

CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (04) :1256-1268

[22] A novel synthesis of 2'-modified 2'-deoxy-4'-thiocytidines from D-glucose [J].

Yoshimura, Y ;

Kitano, K ;

Yamada, K ;

Satoh, H ;

Watanabe, M ;

Miura, S ;

Sakata, S ;

Sasaki, T ;

Matsuda, A .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3140-3152

[23] A novel synthesis of new antineoplastic 2'-deoxy-2'-substituted-4'-thiocytidines [J].