Thiocarbonyl as a Switchable Relay-Auxiliary Group in Carbohydrate Synthesis
A multifunctional O-phenyl thiocarbonyl (O(CS)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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Published in | Organic letters Vol. 23; no. 19; pp. 7313 - 7318 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
01.10.2021
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | A multifunctional O-phenyl thiocarbonyl (O(CS)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. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.1c01968 |