Thiocarbonyl as a Switchable Relay-Auxiliary Group in Carbohydrate Synthesis

A multifunctional O-phenyl thiocarbonyl (O­(CS)­OPh) group was introduced in glycosylation reactions. This auxiliary group exhibits three features (1) C6-long-range participation effect, (2) relay activation, and (3) switchable promoter-controlled carbonylation, which enables the facile synthesis o...

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Bibliographic Details
Published in:Organic letters 2021-10, Vol.23 (19), p.7313-7318
Main Authors: Lin, Mei-Huei, Chang, Chun-Wei, Chiang, Tsun-Yi, Dhurandhare, Vijay M, Wang, Cheng-Chung
Format: Article
Language:English
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Summary:A multifunctional O-phenyl thiocarbonyl (O­(CS)­OPh) group was introduced in glycosylation reactions. This auxiliary group exhibits three features (1) C6-long-range participation effect, (2) relay activation, and (3) switchable promoter-controlled carbonylation, which enables the facile synthesis of both 6-deoxy glucoside and 6-alcohol glucoside. In addition, we successfully quantified the extent of the C6-acyl participation effect and developed its application toward the α-trisaccharide motif.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01968