158213-24-2

Basic information

• Product Name: 2-thiokojibiose
• Synonyms: 2-thiokojibiose
• CAS NO: 158213-24-2
• Molecular Formula: C12H22O10S
• Molecular Weight: 358.36208
• Mol File: 158213-24-2.mol

Chemical Properties

• Boiling Point: 738°C at 760 mmHg
• Flash Point: 400.1°C
• Appearance: /
• Density: 1.77g/cm³
• Vapor Pressure: 3.88E-25mmHg at 25°C
• Refractive Index: 1.691
• CAS DataBase Reference: 2-thiokojibiose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-thiokojibiose(158213-24-2)
• EPA Substance Registry System: 2-thiokojibiose(158213-24-2)

Safety Data

• Hazardous Substances Data: 158213-24-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H22O10S/c13-1-3-6(16)8(18)10(11(20)21-3)23-12-9(19)7(17)5(15)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11+,12-/m1/s1

Upstream product

• 122999-05-7 3,4,5,6-tetra-O-acetyl-1,2-dideoxy-1-nitro-D-arabino-hex-1-enitol 
• 10593-29-0 sodium 1-thio-β-D-glucopyranoside 
• 92051-23-5 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose 
• 18968-05-3 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 62860-10-0 2,3,4,6-tetra-O-acetyl-1-S-acetyl-1-thio-α-D-glucopyranoside 
• 158213-20-8 1,3,4,6-tetra-O-acetyl-2-S-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2-thio-β-D-glucopyranose 
• 158213-21-9 allyl 3,4,6-tri-O-acetyl-2-S-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2-thio-β-D-glucopyranoside 
• 92691-83-3 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranose 
• 92051-24-6 1,3,4,6-tetra-O-acetyl-2-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thio-β-D-glucopyranose 
• 19879-84-6 tetraacetyl thioglucose 

Downstream Products

• 158213-24-2 2-S-β-D-glucopyranosyl-2-thio-β-D-glucopyranose 

Relevant articles and documents

A nitro sugar derivative route to 2-thioepisophorose and 2-thiosophorose and their remarkable facile epimerization

The addition of 1-thio-D-glucose sodium salt to per-O-acetylated 1,2-dideoxy-1-nitro-D-arabino-hex-1-enitol, readily available from D-arabinose, afforded the corresponding 2-S-glycosylated 1-deoxy-1-nitro-D-mannitol and-D-glucitol peracetates. These, after deacetylation, were transformed by the Nef reaction to 2-thioepisophorose and 2-thiosophorose, respectively. The 2-thiodisaccharides easily epimerize in aqueous sodium bicarbonate at ambient temperature to a 1:4 equilibrium mixture. The predominant 2-thiosophorose was obtained crystalline. A 1H NMR study of the epimerization in deuterium oxide showed that the reaction involves an H-2 proton exchange mechanism.

A convenient synthesis for anomeric 2-thioglucobioses, 2-thiokojibiose and 2-thiosophorose

2-S-α-D-Glucopyranosyl-2-thio-D-glucopyranose (2-thiokojibiose, 8) and 2- S-β-D-glucopyranosyl-2-thio-D-glucopyranose (2-thiosophorose, 14) were conveniently prepared by S(N)2 reaction of the corresponding anomers of 2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranose with 1,3,4,6-tetra-O-acetyl-2- O-triflyl-β-D-mannopyranose, followed by a deprotection sequence for the anomeric acetate involving conversion into the 1-propenyl glycosides. Alkaline O-deacetylation was followed by smooth hydrolysis of the propenyl group at pH ~2. 2-S-α-D-Glucopyranosyl-2-thio-D-glucopyranose (2-thiokojibiose, 8) and 2-S-β-D-glucopyranosyl-2-thio-D-glucopyranose (2-thiosophorose, 14) were conveniently prepared by SN2 reaction of the corresponding anomers of 2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranose with 1,3,4,6-tetra-O-acetyl-2-O-triflyl-β-D-mannopyranose, followed by a deprotection sequence for the anomeric acetate involving conversion into the 1-propenyl glycosides. Alkaline O-deacetylation was followed by smooth hydrolysis of the propenyl group at pH approx. 2.

PHASE-TRANSFER CATALYSED SYNTHESIS OF 4-S-β-D-GLUCOPYRANOSYL-4-THIO-D-GLUCOPYRANOSE (THIOCELLOBIOSE) AND 2-S-β-D-GLUCOPYRANOSYL-2-THIO-D-GLUCOPYRANOSE (THIOSOPHOROSE)

Syntheses of the potential enzyme-inducers thiocellobiose (7) and thiosophorose (11) ara described.The intermediates methyl 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-α-D-galactopyranoside and 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethylsulfonyl-β-D-mannopyranose were obtained in good yield from methyl α-D-galactopyranoside or 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose.The stereoselective reaction of triflates with the sodium salt of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose was performed under phase-transfer conditions.Transesterification of methyl 2,3,6-tri-O-benzoyl-4-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-thio-β-D-glucopyranoside (after selective acetolysis) and 1,3,4,6-tetra-O-acetyl-2-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thio-β-D-glucopyranose afforded 7 and 11.