Jump to main content
Jump to site search

Issue 19, 2018
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 25 Feb 2018, accepted on 13 Apr 2018 and first published on 13 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00477C
Citation: Org. Biomol. Chem., 2018,16, 3596-3604
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements