16505-91-2

Basic information

• Product Name: 5-thiohexopyranose
• Synonyms: hexopyranose, 5-thio-
• CAS NO: 16505-91-2
• Molecular Formula: C₆H₁₂O₅S
• Molecular Weight: 196.2215
• Mol File: 16505-91-2.mol

Chemical Properties

• Boiling Point: 401.5°C at 760 mmHg
• Flash Point: 195°C
• Density: 1.744g/cm³
• Vapor Pressure: 4.09E-08mmHg at 25°C
• Refractive Index: 1.707
• CAS DataBase Reference: 5-thiohexopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-thiohexopyranose(16505-91-2)
• EPA Substance Registry System: 5-thiohexopyranose(16505-91-2)

Safety Data

• Hazardous Substances Data: 16505-91-2(Hazardous Substances Data)

Upstream product

• 2816-87-7 1,2-di-O-isopropylidene-5,6-O-thiocarbonyl-α-D-glucofuranose 
• 2946-02-3 1,2-O-isopropylidene-5,6-O-thiocarbonyl-α-D-glucofuranose O-acetate 
• 10227-17-5 3,6-di-O-acetyl-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 103090-82-0 1,2-O:5,6-S,O-di-isopropylidene-5-thio-α-D-ribo-hexofuranos-3-ulose hydrate 
• 72045-04-6 1,2-O-5,6-S,O-di-isopropylidene-5-thio-β-D-allofuranose 
• 72045-06-8 methyl 5-thio-3-o-toluene-p-sulphonyl-α-D-glucopyranoside 
• 72049-05-9 methyl 4,6-O-isopropylidene-5-thio-α-D-altropyranoside 
• 72045-08-0 methyl 2,3-anhydro-4,6-O-isopropylidene-5-thio-α-D-allopyranoside 
• 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 
• 72045-09-1 (4aR,7S,8S,8aS)-6-Methoxy-2,2-dimethyl-hexahydro-thiopyrano[3,2-d][1,3]dioxine-7,8-diol 
• 72074-65-8 methyl 5-thio-α-D-altropyranoside 
• 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 
• 136787-19-4 1,2-O:5,6-S,O-di-isopropylidene-5-thio-β-L-idofuranose 

Downstream Products

• 10470-80-1 1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 10227-18-6 1,2,3,4,6-penta-O-acetyl-5-thio-α-D-glucopyranoside 
• 72045-11-5 2,3:4,6-di-O-isopropylidene-5-thio-α-D-glucopyranose 
• 72045-14-8 1,2:4,6-di-O-isopropylidene-5-thio-α-D-glucopyranose 
• 112254-61-2 (3aR,4S,5aR,9aS,9bS)-4-(1-Methoxy-1-methyl-ethoxy)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]thiopyrano[3,2-d][1,3]dioxine 
• 35827-66-8 1,2,3,4,6-penta-O-acetyl-5-thio-β-D-glucopyranose 

Relevant articles and documents

Thioglucose compound and preparation method thereof

The invention provides a thioglucose compound which has the following general formula: Wherein R is selected from H or acetyl. The preparation method of the thioglucose compound is easy to obtain, low in production cost and suitable for industrial product

Novel SGLT inhibitors

Novel compounds of formula (A) or a pharmaceutically acceptable salt thereof: wherein symbols are as defined in claims, which are useful as SGLT inhibitors and for treatment of diabetes and related diseases.

Synthesis of thiosaccharides employing the Pummerer rearrangement of tetrahydrothiopyran oxides

The Pummerer rearrangement of 1-deoxy-5-thioglucopyranose derivatives carrying acetonides at the C3,4-positions proceeded regioselectively at the C1 position by treating with TFAA in the presence of pyridine. Studies employing deuterium-labelled derivatives revealed that the reaction was induced by E2 1,2-elimination of trifluoroacetic acid of the trifluoroacetoxy sulfonium intermediate. This methodology was applied to the synthesis of an isomaltotriose derivative consisting of 5-thioglucopyranoside units.

Novel synthesis of 5-thio-hexopyranoside: Preparation of 5-thio-D- and L-glucose and 1,6-anhydro-5-thio-L- and D-altrose

Asymmetric synthesis of both D- and L-isomers of 5-thioglucose and 1,6-anhydro-5-thioaltrose are described. The key intermediates, L- and D-threose diethylacetal derivatives, were derived by chemical transformation from D-xylose or D-arabinose and by Sharpless asymmetric dihydroxylation from γ-hydroxycrotylaldehyde diethylacetal. They transformed to γ-thiiranyl diethylacetal via trans-2,3-epoxy alcohol in seven steps. Acetic acid-promoted cyclization of γ-thiiranyl diethylacetal gave 5-thiopyranoside. Removal of the protected groups under the acidic conditions afforded 5-thio-D- and L-glucose and 1,6-anhydro-5-thio-L- and D-altrose, respectively.

Thio-sugars. I. Radical-promoted thione-thiol rearrangement of cyclic thionocarbonates: Synthesis of 5-thioglucose

The 5,6-O-thiocarbonyl-α-D-glucofuranose derivatives 2, when subjected to one of the following reactions, undergo a radical-promoted thione-thiol rearrangement to yield the 5-S-thiolcarbonates of gluco-configuration 8 as the major product. The reactions are, (A) thermolysis with a catalytic amount of tributyltin hydride and AIBN, (B) photolysis with hexabutyldistannane, and (C) thermolysis with dimethyl phosphonate and benzoyl peroxide. On the other hand, thermolysis of 2 with trialkylsilane (condition D) yielded olefins 13 as the major product. The 5-S-gluco product 8 was converted, in three steps, to 5-thioglucose (21) in 55% yield.

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-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

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.

A novel synthesis of 5-thio-D-glucose

A shorter synthesis of 5-thio-D-glucose is described in 8 steps from commercially available D-glucofurano-3,6-lactone.