Glycosyl Nitrates in Synthesis: Streamlined Access to Glucopyranose Building Blocks Differentiated at C-2

Overview

Journal Org Biomol Chem

Publisher Royal Society of Chemistry

Specialties Biochemistry
Chemistry

Date 2018 Apr 26

PMID 29693690

Citations 6

Authors

Tinghua Wang

Swati S Nigudkar

Jagodige P Yasomanee

Nigam P Rath

Keith J Stine

Alexei V Demchenko

Affiliations

Soon will be listed here.

Abstract

In an attempt to refine a CAN-mediated synthesis of 1,3,4,6-tetra-O-acetyl-α-d-glucopyranose (2-OH glucose) we unexpectedly discovered that this reaction proceeds via the intermediacy of glycosyl nitrates. Improved mechanistic understanding of this reaction led to the development of a more versatile synthesis of 2-OH glucose from a variety of precursors. Also demonstrated is the conversion of 2-OH glucose into a variety of building blocks differentially protected at C-2, a position that is generally hard to protect regioselectively in the glucopyranose series.

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