Enantiopure purpurosamine C type glycosyl donors - An improved access from rac-acrolein dimer - Biocatalytic resolution

被引：11

作者：

Erbeck, S ^{[1
]}

Prinzbach, H ^{[1
]}

机构：

[1] UNIV FREIBURG,INST ORGAN CHEM & BIOCHEM,CHEM LAB,D-79104 FREIBURG,GERMANY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 15期

关键词：

AMINOGLYCOSIDE ANTIBIOTICS; PHOTOCHEMICAL ADDITION; BUILDING-BLOCKS; CONFIGURATION; SUGARS; ROUTE;

D O I：

10.1016/S0040-4039(97)00448-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved synthetic access to a suitably ''protected'' purpurosamine C type glycosyl donor (11, analogously ent-ll) starting from racemic 3,4-dihydro-2H-pyran-2-carbaldehyde (rac-1, acrolein dimer) implies an ''indirect aziridination protocol'' and a biocatalytic resolution step (acetate hydrolysis, ee > 98). The latter's stereochemical course is confirmed by a highly ct-selective glycosylation with an acceptor of known absolute configuration. (C) 1997 Elsevier Science Ltd.

引用

页码：2653 / 2656

页数：4

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