10227-19-7

Usage

Molecular weight

204.22 g/mol
Analog of glucose
Sulfur atom replaces oxygen atom at C-1 position of pyranose ring
Used in synthesis of pharmaceuticals and biological probes
Potential antidiabetic and anti-inflammatory properties
Applications in chemical biology and bioorthogonal chemistry
Versatile and important in scientific research and medical advancements

Upstream product

• 136787-19-4 1,2-O:5,6-S,O-di-isopropylidene-5-thio-β-L-idofuranose 
• 72074-65-8 methyl 5-thio-α-D-altropyranoside 
• 72045-09-1 (4aR,7S,8S,8aS)-6-Methoxy-2,2-dimethyl-hexahydro-thiopyrano[3,2-d][1,3]dioxine-7,8-diol 
• 72045-08-0 methyl 2,3-anhydro-4,6-O-isopropylidene-5-thio-α-D-allopyranoside 
• 72049-05-9 methyl 4,6-O-isopropylidene-5-thio-α-D-altropyranoside 
• 72045-04-6 1,2-O-5,6-S,O-di-isopropylidene-5-thio-β-D-allofuranose 
• 103090-82-0 1,2-O:5,6-S,O-di-isopropylidene-5-thio-α-D-ribo-hexofuranos-3-ulose hydrate 
• 72045-06-8 methyl 5-thio-3-o-toluene-p-sulphonyl-α-D-glucopyranoside 
• 72045-07-9 methyl 4,6-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucopyranoside 
• 50680-04-1 6-O-acetyl-5-S-acetyl-1,2-O-isopropylidene-5-thio-3-toluene-p-sulphonyl-α-D-glucofuranose 
• 136787-18-3 Methanesulfonic acid (3aR,5S,6R,6aR)-5-((S)-2,2-dimethyl-[1,3]oxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

Relevant academic research and scientific papers

Synthesis of derivatives of 5-thio-L-idose

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

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.

SYNTHESIS OF 5-THIO-D-ALTROSE AND SOME OF ITS DERIVATIVES

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