Regioselective 1-O-Acyl Hydrolysis of Peracylated Glycopyranoses by Mercuric Chloride and Mercuric Oxide

Thota Sambaiah; Phillip E. Fanwick; Mark Cushman

doi:10.1055/s-2001-16084

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Synthesis 2001(10): 1450-1452
DOI: 10.1055/s-2001-16084

SHORTPAPER

Regioselective 1-O-Acyl Hydrolysis of Peracylated Glycopyranoses by Mercuric Chloride and Mercuric Oxide

Thota Sambaiah^a, Phillip E. Fanwick^b, Mark Cushman*^a
^a Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907, USA
Fax: +1(765)4946790; e-Mail: cushman@pharmacy.purdue.edu;
^b Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA

Further Information

Publication History

Received 19 January 2001
Publication Date:
23 September 2004 (online)

Abstract
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Abstract

A convenient synthetic method for regioselective 1-O-acyl hydrolysis of peracylated glycopyranoses into tetra-O-acylglycopyranoses using mercuric chloride and mercuric oxide in aqueous acetone is described.

Key words

glycopyranoses - oligosaccharides - regioselectivity - stereoselectivity - mercuric chloride

References

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13

Selected bond lengths (Å) and angles (°) of 9: O(1)-C(2) 1.409(2), O(21)-C(2) 1.420(2), O(31)-C(3) 1.444(2), O(41)-C(4) 1.442(2), O(51)-C(5) 1.441(2), C(6)-C(61) 1.521(3), O(21)-C(22) 1.363(2), C(3)-C(2) 1.515(2), O(1)-C(2)-O(21) 107.36(14), O(1)-C(2)-C(3) 105.04(14), O(1)-C(6)-C(5) 110.38(14), O(41)-C(4)-C(5) 110.35(14), C(3)-C(4)-C(5) 110.70(14), C(22)-O(21)-C(2) 118.03(13), C(32)-O(31)-C(3) 117.58(13), C(42)-O(41)-C(4) 118.69(13), C(2)-O(1)-C(6) 111.21(13).