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

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.

glycopyranoses - oligosaccharides - regioselectivity - stereoselectivity - mercuric chloride

References

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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).

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