Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH(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(4) and aryl dis...

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Detalles Bibliográficos
Autores principales: Guo, Yang-Fan, Luo, Tao, Feng, Guang-Jing, Liu, Chun-Yang, Dong, Hai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9506437/
https://www.ncbi.nlm.nih.gov/pubmed/36144712
http://dx.doi.org/10.3390/molecules27185980
Descripción
Sumario: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(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.

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