Glycosyl Formates: Glycosylations with Neighboring-Group Participation

Protected 2-O-benzyolated glycosyl formates were synthesized in one-step from the corresponding orthoester using formic acid as the sole reagent. Glucopyranosyl, mannopyranosyl and galactopyranosyl donors were synthesized and their glycosylation properties studied using model glycosyl acceptors of v...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-09, Vol.27 (19), p.6244
Main Authors: Yang, Liang, Pedersen, Christian Marcus
Format: Article
Language:English
Subjects:
Acids
atom economy
Bismuth
catalysis
Catalysts
Fluorides
Formates
Formic acid
Glycosylation
Investigations
neighboring-group participation
Reagents
selectivity
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Summary:Protected 2-O-benzyolated glycosyl formates were synthesized in one-step from the corresponding orthoester using formic acid as the sole reagent. Glucopyranosyl, mannopyranosyl and galactopyranosyl donors were synthesized and their glycosylation properties studied using model glycosyl acceptors of varied steric bulk and reactivity. Bismuth triflate was the preferred catalyst and KPF6 was used as an additive. The 1,2-trans-selectivities resulting from neighboring-group participation were excellent and the glycosylations were generally high-yielding.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27196244