Synthesis of long-chain monosaccharides via the coupling of three 'normal' sugar units via Wittig type methodology: unusual removal of the benzyl group under basic conditions

被引：3

作者：

Cieplak, Maciej ^{[1
]}

Jarosz, Slawomir ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 18-19期

关键词：

HIGHER CARBON SUGARS; ALLYLIC ALCOHOLS; HIGH-PRESSURE; DERIVATIVES; 1-METHOXYBUTA-1,3-DIENE; STEREOCHEMISTRY; ALDEHYDES; ROUTE; ACIDS;

D O I：

10.1016/j.tetasy.2011.10.001

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reaction of diacetonogalactose phosphonate 6 with 2,3:4,5-di-O-isopropylidene-D-arabinose (7) afforded C-12-higher sugar enone with an E-geometry across the double bond, which was converted into the fully protected C-11-aldehyde 16. This compound was very unreactive and resistant toward the Wittig type and Tebbe reagents, but under PTC conditions, underwent a reaction with stabilized sugar phosphonate to afford C-18-enone 17. Very surprisingly unusual removal of the benzyl blocks under these conditions was observed. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1757 / 1762

页数：6

共 38 条

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