β-glycosidation of sterically hindered alcohols

Alex M. Szpilman; Erick M. Carreira

doi:10.1021/ol9000735

β-glycosidation of sterically hindered alcohols

Alex M. Szpilman, Erick M. Carreira

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

The 2-chloro-2-methylpropanoic ester serves as a steering group in the Schmidt glycosidation reaction. Rapid and efficient glycosidation of a range of sterically hindered alcohols takes place under mild, acidic conditions to afford the glycoside products in high yield and β-selectivity and without formation of orthoester side products. The 2-chloro-2-methylpropanoic ester is readily cleaved under mild, basic conditions.

Original language	English
Pages (from-to)	1305-1307
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	6
DOIs	https://doi.org/10.1021/ol9000735
State	Published - 19 Mar 2009
Externally published	Yes

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10.1021/ol9000735

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abstract = "The 2-chloro-2-methylpropanoic ester serves as a steering group in the Schmidt glycosidation reaction. Rapid and efficient glycosidation of a range of sterically hindered alcohols takes place under mild, acidic conditions to afford the glycoside products in high yield and β-selectivity and without formation of orthoester side products. The 2-chloro-2-methylpropanoic ester is readily cleaved under mild, basic conditions.",

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AB - The 2-chloro-2-methylpropanoic ester serves as a steering group in the Schmidt glycosidation reaction. Rapid and efficient glycosidation of a range of sterically hindered alcohols takes place under mild, acidic conditions to afford the glycoside products in high yield and β-selectivity and without formation of orthoester side products. The 2-chloro-2-methylpropanoic ester is readily cleaved under mild, basic conditions.

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β-glycosidation of sterically hindered alcohols

Abstract

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