Synthesis of 5-thio-d-allose and the methyl 5-thio-α- and -β-d-allopyranosides☆

Add time:09/08/2019    Source:sciencedirect.com

5,6-Anhydro-1,2-O-isopropylidene-3-O-methanesulphonyl-α-d-idofuranose was converted, via the related gluco-5,6-episulphide, into 6-O-acetyl-5-S-acetyl-1,2-O-isopropylidene-3-O-methanesulphonyl-5- thio-α-d-glucofuranose (9). Replacement of the acetyl groups of 9, or the related 3-toluene-p-sulphonate, by an isopropylidene group and saponification of the sulphonate group gave 1,2-O:5,6-S,O-di-isopropylidene-5-thio-α-d-glucofuranose (2). Epimerisation at C-3 of 2 by an oxidation-reduction sequence gave 1,2-O:5,6-S,O-di-isopropylidene-5-thio-α-d-allofuranose (20) which was hydrolysed to 5-thio-d-allose (1). Methyl 5-thio-α-and -β-d-allopyranoside were obtained from 1 or by methanolysis of 20. Similar hydrolysis or methanolysis of 2 gave 5-thio-d-glucose or methyl 5-thio-α- and -β-d-glucopyranoside, respectively, thus providing a convenient variation on earlier synthetic routes to these compounds. 13C-N.m.r. data are given for several of these 5-thio-allo and -gluco derivatives.

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