Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH4

An improved method to efficiently synthesize 2-OH thioaryl glycosides starting from corresponding per-protected glycals was developed, where 1,2-anhydro sugars were prepared by the oxidation of glycals with oxone, followed by reaction of crude crystalline 1,2-anhydro sugars with NaBH4 and aryl disul...

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Published inMolecules (Basel, Switzerland) Vol. 27; no. 18; p. 5980
Main Authors Guo, Yang-Fan, Luo, Tao, Feng, Guang-Jing, Liu, Chun-Yang, Dong, Hai
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 14.09.2022
MDPI
Subjects
2-OH thioglycosides
glycals
glycosyl donors
glycosylation
Methods
one-pot reaction
Oxidation
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Summary:An improved method to efficiently synthesize 2-OH thioaryl glycosides starting from corresponding per-protected glycals was developed, where 1,2-anhydro sugars were prepared by the oxidation of glycals with oxone, followed by reaction of crude crystalline 1,2-anhydro sugars with NaBH4 and aryl disulfides. This method has been further used in a one-pot reaction to synthesize glycosyl donors having both “armed” and “NGP (neighboring group participation)” effects.
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These authors contributed equally to this work.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27185980