Dehydrative glycosylation with cyclic phosphonium anhydrides

Cyclic phosphonium anhydrides generated from bis-phosphine oxides and trifluoromethanesulfonic anhydride are shown as general coupling reagents in a dehydrative glycosylation reaction of C1-hemiacetals. This reaction protocol is characterized by a broad substrate scope and high yields, including rea...

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Published inOrganic & biomolecular chemistry Vol. 15; no. 1; pp. 51 - 55
Main Authors Dyapa, Rajendar, Dockery, Lance T., Walczak, Maciej A.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GLYCOSIDES
BETA-MANNOPYRANOSIDES
ACTIVATION
ANOMERIC HYDROXY SUGARS
HENDRICKSON POP REAGENT
BOND FORMATION
AUTOMATED OLIGOSACCHARIDE SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
SULFOXIDE METHOD
TRIFLUOROMETHANESULFONIC ANHYDRIDE
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Summary:Cyclic phosphonium anhydrides generated from bis-phosphine oxides and trifluoromethanesulfonic anhydride are shown as general coupling reagents in a dehydrative glycosylation reaction of C1-hemiacetals. This reaction protocol is characterized by a broad substrate scope and high yields, including reactions of O-, C-, N-, and S-based nucleophiles with furanose, pyranose, and deoxysugar donors.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01812b