53269-96-8

Basic information

• Product Name: O-ethyl S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl) dithiocarbonate
• Synonyms: O-ethyl S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl) dithiocarbonate
• CAS NO: 53269-96-8
• Molecular Weight: 644.853
• Mol File: 53269-96-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: O-ethyl S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl) dithiocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: O-ethyl S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl) dithiocarbonate(53269-96-8)
• EPA Substance Registry System: O-ethyl S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl) dithiocarbonate(53269-96-8)

Safety Data

• Hazardous Substances Data: 53269-96-8(Hazardous Substances Data)

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 4291-68-3 1-chloro-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 140-89-6 potassium ethyl xanthogenate 
• 79386-43-9 diphenyl 2,3,4,6-tetra-O-benzyl-α-D-glucosyl phosphate 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 

Downstream Products

• 149440-92-6 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide 
• 72174-24-4 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 118206-39-6 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone 
• 141561-29-7 Bis(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-disulfid 

Relevant articles and documents

Glucose-based spiro-oxathiazoles as: In vivo anti-hyperglycemic agents through glycogen phosphorylase inhibition

The design of glycogen phosphorylase (GP) inhibitors targeting the catalytic site of the enzyme is a promising strategy for a better control of hyperglycaemia in the context of type 2 diabetes. Glucopyranosylidene-spiro-heterocycles have been demonstrated as potent GP inhibitors, and more specifically spiro-oxathiazoles. A new synthetic route has now been elaborated through 1,3-dipolar cycloaddition of an aryl nitrile oxide to a glucono-thionolactone affording in one step the spiro-oxathiazole moiety. The thionolactone was obtained from the thermal rearrangement of a thiosulfinate precursor according to Fairbanks' protocols, although with a revisited outcome and also rationalised with DFT calculations. The 2-naphthyl substituted glucose-based spiro-oxathiazole 5h, identified as one of the most potent GP inhibitors (Ki = 160 nM against RMGPb) could be produced on the gram-scale from this strategy. Further evaluation in vitro using rat and human hepatocytes demonstrated that compound 5h is a anti-hyperglycaemic drug candidates performing slightly better than DAB used as a positive control. Investigation in Zucker fa/fa rat model in acute and subchronic assays further confirmed the potency of compound 5h since it lowered blood glucose levels by ～36% at 30 mg kg-1 and ～43% at 60 mg kg-1. The present study is one of the few in vivo investigations for glucose-based GP inhibitors and provides data in animal models for such drug candidates.

Nucleophilic Substitution of Tetra-O-benzyl-α-D-glucopyranosyl 1-O-Phosphate under Phase-transfer Catalysed Conditions

An efficient conversion of tetra-O-benzyl-α-D-glucopyranosyl 1-O-phosphate into corresponding 1-thiosugar derivatives, O-aryl glycosides and azides have been described.Reactions were performed under Phase-Transfer Catalysed conditions or in a Catalytic-Tw

Synthesis of glycosyl xanthates from reducing sugar derivatives under phase-transfer conditions

-