Journal
MOLECULES
Volume 27, Issue 19, Pages -Publisher
MDPI
DOI: 10.3390/molecules27196244
Keywords
glycosylation; catalysis; selectivity; formates; neighboring-group participation; atom economy
Funding
- China Scholarship Council [201806220084]
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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 were studied. Bismuth triflate was the preferred catalyst and KPF6 was used as an additive. The glycosylations showed excellent 1,2-trans-selectivities and high yields.
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.
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