Selective Synthesis of 1,2-cis-α-Glycosides without Directing Groups. Application to Iterative Oligosaccharide Synthesis

Selective Synthesis of 1,2-cis-α-Glycosides without Directing Groups. Application to Iterative Oligosaccharide Synthesis
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DOI:
10.1021/ol401095k
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发表时间:
2013-05-17
期刊:
影响因子:
5.2
通讯作者:
Bennett, Clay S.
Bennett, Clay S.
中科院分区:
化学1区
文献类型:
--
作者:
Chu, An-Hsiang Adam;Son Hong Nguyen;Bennett, Clay S.

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描述了一种高选择性合成1,2-顺式- α -连接糖苷的方法,该方法不需要使用通常用于控制非对映选择性的特殊保护基团模式。巯基糖苷受体可以使用,允许迭代低聚糖合成。这种方法消除了长时间合成具有高度专业化和非常规保护基团模式的单糖的需要。
A method for the highly selective synthesis of 1,2-cis-alpha-linked glycosides that does not require the use of the specialized protecting group patterns normally employed to control diastereoselectivity is described. Thioglycoside acceptors can be used, permitting iterative oligosaccharide synthesis. The approach eliminates the need for lengthy syntheses of monosaccharides possessing highly specialized and unconventional protecting group patterns.