Glycosyl nitrates in synthesis: streamlined access to glucopyranose building blocks differentiated at C-2.

ABSTRACT: In an attempt to refine a CAN-mediated synthesis of 1,3,4,6-tetra-O-acetyl-?-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.

SUBMITTER: Wang T 

PROVIDER: S-EPMC5971085 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature