Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH[sub.4]

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 NaBH[sub.4] and aryl...

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Published inMolecules (Basel, Switzerland) Vol. 27; no. 18
Main Authors Guo, Yang-Fan, Luo, Tao, Feng, Guang-Jing, Liu, Chun-Yang, Dong, Hai
Format Journal Article
LanguageEnglish
Published MDPI AG 01.09.2022
Subjects
Chemical synthesis
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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 NaBH[sub.4] 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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27185980