Silyl-protective groups influencing the reactivity and selectivity in glycosylations.
Silyl-protective groups influencing the reactivity and selectivity in glycosylations.
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DOI：
10.3762/bjoc.13.12
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发表时间：
2017
影响因子：
2.7
通讯作者：
Pedersen CM
中科院分区：
文献类型：
--
作者：
Bols M;Pedersen CM
甲硅烷基基团如TBDPS、TBDMS、TIPS或TMS是有机化学中熟知且广泛使用的醇保护基团。环状亚甲硅烷基保护基团也变得越来越受欢迎。在碳水化合物化学中，甲硅烷基保护基经常主要用作更常用的酰基和苄基保护基的正交保护基。然而，甲硅烷基保护基团具有与酰基和烷基保护基团显著不同的电子和空间要求，这在两个或更多个相邻醇被甲硅烷基保护时变得特别重要。在过去的十年中，已经发现多硅烷化糖基供体具有不寻常的性质，例如高（或低）反应性或高立体选择性。这篇小综述将总结这些发现。
Silyl groups such as TBDPS, TBDMS, TIPS or TMS are well-known and widely used alcohol protective groups in organic chemistry. Cyclic silylene protective groups are also becoming increasingly popular. In carbohydrate chemistry silyl protective groups have frequently been used primarily as an orthogonal protective group to the more commonly used acyl and benzyl protective groups. However, silyl protective groups have significantly different electronic and steric requirements than acyl and alkyl protective groups, which particularly becomes important when two or more neighboring alcohols are silyl protected. Within the last decade polysilylated glycosyl donors have been found to have unusual properties such as high (or low) reactivity or high stereoselectivity. This mini review will summarize these findings.