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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

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

Wang Tinghua T Nigudkar Swati S SS Yasomanee Jagodige P JP Rath Nigam P NP Stine Keith J KJ Demchenko Alexei V AV

Organic & biomolecular chemistry 20180501 19

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 gener ...[more]

PMID: 29693690

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