Synthesis of 5-epi-deoxynojirimycin from methyl α-D-glucoside

被引：4

作者：

Witkowski, Grzegorz ^{[1
]}

Kowalski, Michal ^{[1
]}

Szyszka, Lukasz ^{[1
]}

Potopnyk, Mykhaylo A. ^{[1
]}

Jarosz, Slawomir ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 16期

关键词：

POLYHYDROXYLATED PIPERIDINE; BICYCLIC IMINOSUGARS; DERIVATIVES; INHIBITORS; ALKALOIDS; OXIDATION; RING;

D O I：

10.1016/j.tetasy.2016.06.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A simple method for the preparation of 5-epi-nojirymycin (5-epi-DNJ) by a reductive amination of sugar derived alkoxyamines is presented. The latter were prepared in situ from the respective alkylated sugar oximes, which were obtained from the readily available methyl alpha-D-glucoside in a few well defined steps. The stereoselectivity of the reductive amination/cyclisation step depended on the size of the alkyl group in the oxime moiety and was best for the derivative decorated with a bulky tert-butoxyl group (5-epi-DNJ:DNJ = 82:18). The stereochemical outcome of this reaction was rather surprising since the analogous process performed for sugar alkylamines usually provides predominantly derivatives of DNJ. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：747 / 752

页数：6

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