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Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation.

ABSTRACT: Glycosyl triflates with a 2,3-oxazolidinone protecting group were generated from thioglycosides by low-temperature electrochemical oxidation. The glycosyl triflates reacted with alcohols to give the corresponding glycosides ?-selectively at low temperatures. However, ?-selectivity was observed in the absence of base at elevated reaction temperatures. In situ generated triflic acid promotes the isomerization of ?-products to ?-products.

SUBMITTER: Nokami T

PROVIDER: S-EPMC3326625 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation.

Nokami Toshiki T Shibuya Akito A Saigusa Yoshihiro Y Manabe Shino S Ito Yukishige Y Yoshida Jun-Ichi J

Beilstein journal of organic chemistry 20120328

Glycosyl triflates with a 2,3-oxazolidinone protecting group were generated from thioglycosides by low-temperature electrochemical oxidation. The glycosyl triflates reacted with alcohols to give the corresponding glycosides β-selectively at low temperatures. However, α-selectivity was observed in the absence of base at elevated reaction temperatures. In situ generated triflic acid promotes the isomerization of β-products to α-products. ...[more]

PMID: 22509217

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