C. Mamat, T. Peppel, M. Köckerling
Feb 29, 2012
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Abstract
Abstract: The crystal and molecular structure of 1,2:5,6-di- O -isopropylidene-3- O -toluenesulfonyl-α- D -glucofuranose is reported. This compound crystallizes from a petroleum ether/ethyl acetate mixture with the chiral orthorhombic space group P2 1 2 1 2 1 with four molecules in the unit cell. The unit cell parameters are: a = 9.7945(7) A, b = 10.1945(7) A, c = 21.306(1) A, and V = 2127.4(2) A 3 . No classical hydrogen bonds were found. Bond lengths and angles of this tosylated glucofuranose derivative are typical. Keywords: carbohydrates; glucose; tosylation 1. Introduction Monosaccharides with good leaving groups like mesylate, tosylate or nosylate play a major role for the introduction of various functional groups, as building blocks for the formation of di- and oligosugars, as chiral pool materials or for the preparation of bioactive glycoconjugates [1]. This offers the possibility for the preparation of rare carbohydrate derivatives. For this purpose, protected carbohydrate building blocks like carbohydrate