Pd-catalyzed coupling reaction of glycosylamines with 6-chloropurines:: Synthesis of 6-(β-D-mannopyranosylamino)-9H-purine and its β-D-gluco isomer, N-glycoside models for spicamycin and septacidin

被引：27

作者：

Chida, N ^{[1
]}

Suzuki, T ^{[1
]}

Tanaka, S ^{[1
]}

Yamada, I ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(99)00250-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of preparation of 6-(beta-D-mannopyranosylamino)-9H-purine (8), whose N-glycosidic linkage corresponds to a natural antibiotic, spicamycin, by Pd-catalyzed coupling reaction of a mannopyranosylamine with 9-protected-6-chloropurine, followed by deprotection, is described. Its beta-D-gluco isomer (11) was also synthesized. This work established the procedure to construct the novel N-glycoside, in which the pyranose unit is connected to the amino group at C(6) of adenine moiety. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2573 / 2576

页数：4

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