β-L-Rhamnosylation and β-D-Mannosylation Mediated by 4-O-Ester Groups in Weakly Nucleophilic Environment

04 August 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Eq-4-O-acyl group directed β-rhamnosylation and β-mannosylation are achieved in carborane or BARF anion formed weakly nucleophilic environment with the assistance of a 2,3-orthocarbonate group. The 4-O-acyl group plays a critical role in directing the β-selectivity, and the weakly coordinating anion is essential to amplify this direction. The orthocarbonate group could be readily removed with 1,3-propanediol in the presence of BF3.Et2O.

Keywords

Glycosylation
Neighboring group participation
Non-coordinating anion
β-rhamnosylation
β-mannosylation

Supplementary materials

Title
Description
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Supporting Information
Description
General procedure, optimization details, characterization data, crystallographic data, and NMR spectra.
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