Synthesis of nojirimycin C-glycosides

被引：26

作者：

Cipolla, L ^{[1
]}

Palma, A ^{[1
]}

La Ferla, B ^{[1
]}

Nicotra, F ^{[1
]}

机构：

[1] Univ Milano Bicocca, Dept Biosci & Biotechnol, I-20126 Milan, Italy

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 19期

关键词：

D O I：

10.1039/b206623h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nojirimycin alpha-C-glycosides, which have 1-alpha-allyl-1-deoxy-N-benzyl-2,3,4,6-tetra-O-benzylnojirimycin (9) as a key intermediate for further derivatisation, have been synthesized from commercially available 2,3,4,6-tetra-O-benzyl-glucopyranose (3) through a highly stereoselective procedure which involves treatment of 3 with benzylamine, reaction of the obtained glucosylamine 4 with allylmagnesium bromide and cyclization of the elongated open-chain aminosugar 5 by Fmoc-protection, oxidation of the free hydroxy group, and intramolecular reductive-amination, affording 9 in 59% overall yield. The efficient manipulation of the allylic appendage of 9 has required N-debenzylation and Fmoc-protection of the ring-nitrogen.

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页码：2161 / 2165

页数：5

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