Operationally simple enzymatic deprotection of C-3 position on 3,4,6-tri-O-acetyl-d-glucal

Abstract

The new strategies to obtain selectively protected hydroxyl function on sugar derivatives are still of the high value for the progress of glycochemistry and organic synthesis. Herein, we describe an interesting enzymatic deprotection strategy that was applied to the most commonly used glycal derivative - 3,4,6-tri-O-acetyl-d-glucal. The procedure is operationally simple, easy to scale-up and the biocatalyst might be effortlessly recycled from the reaction mixture. Resulting product - 4,6-di-O-acetyl-D-glucal we then challenged to synthesize two glycal synthons armed with 3 different protecting group - a synthetic target difficult to achieve with traditional methods.

Keywords: Biocatalysis; D-glucal; Enzymatic reactions; Glycals; Protecting group strategies.