Glycosyl Formates: Glycosylations with Neighboring-Group Participation
Liang Yang1, Christian Marcus Pedersen1
1Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø, Denmark.
Abstract:
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.
Related Concept Videos
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
Oligosaccharide Assembly
Multiple sugar molecules that may or may...
Proteoglycans
Protein Glycosylation
Glycosylation occurs in...
Organic Compounds
Esters to Alcohols: Grignard Reaction
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...


