37850-98-9Relevant academic research and scientific papers
SYNTHESIS OF 5-THIO-D-ALTROSE AND SOME OF ITS DERIVATIVES
Al-Masoudi, Najim A. L.,Hughes, Neil A.
, p. 39 - 50 (1986)
Acid-catalysed methanolysis of 6-O-acetyl-5-S-acetyl-1,2-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucofuranose gave the methyl 5-thio-3-O-toluene-p-sulphonyl-α- and -β-D-glucopyranosides (5).Treatment of 5 with acidified 2,2-dimethoxypropane a
Synthesis of derivatives of 5-thio-L-idose
Hughes, Neil A.,Munkombwe, Namboole M.,Todhunter, Nigel D.
, p. 119 - 128 (2007/10/02)
1,2-O:5,6-S,O-Di-isopropylidene-5-thio-β-L-idofuranose (6) was synthesised from 1,2-O-isopropylidene-3,5,6-tri-O-methanesulphonyl-α-D-glucofuranose (1).Hydrolysis of 6 yielded 5-thio-L-idose (11) and 1,6-anhydro-5-thio-β-L-idopyranose (13), characterised
SYNTHESIS OF 5-THIO-D-ALLOSE AND THE METHYL 5-THIO-α- AND -β-D-ALLOPYRANOSIDES
Al-Masoudi, Najim A. L.,Hughes, Neil A.
, p. 25 - 38 (2007/10/02)
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-isoprpylidene-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 varation on earlier synthetic routes to these compounds. 13C N.m.r. data are given for several of these 5-thio-allo and -gluco derivatives.
