ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations

An efficient and versatile glycosylation methodology is crucial for the systematic synthesis of oligosaccharides and glycoconjugates. A direct intermolecular and an indirect intramolecular methodology have been developed, and the former can be applied to the synthesis of medium-to-long-chain glycans...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2024-10, Vol.29 (19), p.4710
Main Authors: Ishiwata, Akihiro, Zhong, Xuemei, Tanaka, Katsunori, Ito, Yukishige, Ding, Feiqing
Format: Article
Language:English
Subjects:
1,2-cis-glycoside
constrained glycosyl donors
oligosaccharides
Participation
Review
stereoselective cis-glycosylation
ZnI2
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Summary:An efficient and versatile glycosylation methodology is crucial for the systematic synthesis of oligosaccharides and glycoconjugates. A direct intermolecular and an indirect intramolecular methodology have been developed, and the former can be applied to the synthesis of medium-to-long-chain glycans like that of nucleotides and peptides. The development of a generally applicable approach for the stereoselective construction of glycosidic bonds remains a major challenge, especially for the synthesis of 1,2-cis glycosides such as β-mannosides, β-L-rhamnosides, and β-D-arabinofuranosides with equatorial glycosidic bonds as well as α-D-glucosides with axial ones. This review introduces the direct formation of cis-glycosides using ZnI2-mediated cis-glycosylations of various constrained glycosyl donors, as well as the recent advances in the development of stereoselective cis-glycosylations.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29194710