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Glycosyl Formates: Glycosylations with Neighboring-Group Participation.

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.

SUBMITTER: Yang L

PROVIDER: S-EPMC9572138 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Glycosyl Formates: Glycosylations with Neighboring-Group Participation.

Yang Liang L Pedersen Christian Marcus CM

Molecules (Basel, Switzerland) 20220922 19

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 KPF<sub>6</sub> was used as an additive. The 1,2-trans-selectivities resulting from neighboring-group participation we ...[more]

PMID: 36234778

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