Allyl protecting group mediated intramolecular aglycon delivery: optimisation of mixed acetal formation and mechanistic investigation

被引：28
作者：
Cumpstey, I
Chayajarus, K
Fairbanks, AJ
Redgrave, AJ
Seward, CMP
机构：
[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 20期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1016/j.tetasy.2004.09.003
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An efficient protocol for the formation of alpha-iodo mixed acetals, the first step of allyl-mediated 1AD, by reaction of allyl-derived enol ethers and alcohols, using I-2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, is reported. This reagent combination is capable of tethering glycosyl donors to the secondary alcohol groups of a variety of glycosyl acceptors including mono-, di- and trisaccharides. Mechanistic studies confirm the intramolecular nature of the glycosylation reaction, whilst the attempted use of diol glycosyl acceptors reveals limitations of both regio- and stereo selectivity in the glycosylation step. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3207 / 3221
页数：15
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