Stereoselective Synthesis of 2-Deoxythiosugars from Glycals.

Content Provider	Europe PMC
Author	You, Xueying Cai, Yifei Xiao, Chenyu Ma, Lijuan Wei, Yong Xie, Tianpeng Chen, Lei Yao, Hui
Editor	Yin, Jian Zeng, Jing Xiong, De-Cai
Copyright Year	2022
Abstract	2-deoxythiosugars are more stable than 2-deoxysugars occurring broadly in bioactive natural products and pharmaceutical agents. An effective and direct methodology to stereoselectively synthesize α-2-deoxythioglycosides catalyzed by AgOTf has been developed. Various alkyl thiols and thiophenols were explored and the desired products were formed in good yields with excellent α-selectivity. This method was further applied to the syntheses of S-linked disaccharides and late-stage 2-deoxyglycosylation of estrogen, L-menthol, and zingerone thiols successfully.
Journal	Molecules
Volume Number	27
DOI	10.3390/molecules27227979
PubMed Central reference number	PMC9696349
Issue Number	22
PubMed reference number	36432078
e-ISSN	14203049
Language	English
Publisher	Molecular Diversity Preservation International (MDPI)
Publisher Date	2022-11-17
Access Restriction	Open
Subject Keyword	2-deoxythioglycosides glycosylation silver triflate stereoselective synthesis glycals
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Medicine Chemistry Drug Discovery Pharmaceutical Science Analytical Chemistry Molecular Medicine Organic Chemistry