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Issue 19, 2018
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Glycosyl nitrates in synthesis: streamlined access to glucopyranose building blocks differentiated at C-2

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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.

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

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Article information


Submitted
25 Feb 2018
Accepted
13 Apr 2018
First published
13 Apr 2018

Org. Biomol. Chem., 2018,16, 3596-3604
Article type
Paper

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

T. Wang, S. S. Nigudkar, J. P. Yasomanee, N. P. Rath, K. J. Stine and A. V. Demchenko, Org. Biomol. Chem., 2018, 16, 3596
DOI: 10.1039/C8OB00477C

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