立体选择性
化学
SN2反应
位阻效应
糖基
电泳剂
亲核细胞
立体化学
糖基化
硅烷化
有机化学
催化作用
生物化学
作者
Kaname Sasaki,Nanako Uesaki
出处
期刊:Advances in Carbohydrate Chemistry and Biochemistry
日期:2022-01-01
卷期号:: 107-155
被引量:2
标识
DOI:10.1016/bs.accb.2022.10.005
摘要
In nucleophilic reactions using sugars as electrophiles, i.e., glycosyl donors, their conformation affects the generation rate or stability of the glycosyl cation intermediates and determines at which side of the SN2–SN1 borderline and at what rate the reaction occurs. In addition, changes in the conformation create the steric or stereoelectronic effects of the substituents, which also change the reaction rate and stereoselectivity. Bulky silyl protecting groups, uronic acid esters, and transannular structures have been utilized to change the conformation. Consequently, reactions with unique reactivities and stereoselectivities have been developed. In this chapter, a discussion of the reaction mechanisms relating stereoselectivity to conformation is provided.
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