Propargyl 1,2-orthoesters for stereoselective synthesis of thioglycosides and 1-thiotrehaloses

•Various thiosaccharides and 1-thiotrehaloses were synthesized.•Salient features of gold-catalyzed glycosidation were applied.•Alkynyl 1,2-orthoesters as glycosyl donors were exploited.•The reaction was found to be general, high yielding, diastereoselective, fast, mild and catalytic. [Display omitte...

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Bibliographic Details
Published in:	Carbohydrate research Vol. 417; pp. 103 - 108
Main Authors:	Venkateswara Rao, Boddu, Manmode, Sujit, Hotha, Srinivas
Format:	Journal Article
Language:	English
Published:	Netherlands Elsevier Ltd 19-11-2015
Subjects:	1-Thiotrehaloses Catalysis Esters Gold - chemistry Gold catalysis Green Chemistry Technology Molecular Structure Orthoesters Stereoisomerism Sulfhydryl Compounds - chemistry Thioglycosides Thioglycosides - chemical synthesis Trehalose - chemical synthesis Gold catalysis 1-Thiotrehaloses Orthoesters Thioglycosides
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Summary:	•Various thiosaccharides and 1-thiotrehaloses were synthesized.•Salient features of gold-catalyzed glycosidation were applied.•Alkynyl 1,2-orthoesters as glycosyl donors were exploited.•The reaction was found to be general, high yielding, diastereoselective, fast, mild and catalytic. [Display omitted] Various thiosaccharides and 1-thiotrehaloses were synthesized exploiting salient features of gold-catalyzed glycosidation repertoire using alkynyl 1,2-orthoesters as glycosyl donors. The reaction was found to be general, high yielding, diastereoselective, fast, mild and catalytic.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0008-6215 1873-426X
DOI:	10.1016/j.carres.2015.09.009