286369-06-0

Basic information

• Product Name: C-(2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL) FORMAMIDE
• Synonyms: C-(2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL) FORMAMIDE;C-(2,3,4,6-TETRA-O-BENZOYL-SS-D-GLUCOPYRANOSYL) FORMAMIDE
• CAS NO: 286369-06-0
• Molecular Formula: C₃₅H₂₉NO₁₀
• Molecular Weight: 623.60546
• Mol File: 286369-06-0.mol

Chemical Properties

• Boiling Point: 803.6±65.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• PKA: 14.98±0.70(Predicted)
• CAS DataBase Reference: C-(2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL) FORMAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: C-(2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL) FORMAMIDE(286369-06-0)
• EPA Substance Registry System: C-(2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL) FORMAMIDE(286369-06-0)

Safety Data

• Hazardous Substances Data: 286369-06-0(Hazardous Substances Data)

Upstream product

• 286369-05-9 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl cyanide 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 67-64-1 acetone 

Downstream Products

• 262849-68-3 C-(2,3,4,6-tetra-O-benzoyl-1-bromo-1-deoxy-β-D-glucopyranosyl)formamide 
• 848034-51-5 (2R,3R,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-2-carboxylic acid 
• 848034-52-6 methyl 2,6-anhydro-3,4,5,7-tetra-O-benzoyl-D-glycero-D-gulo-heptonate 
• 848034-66-2 methyl 3,4,5,7-tetra-O-benzoyl-2-bromo-2-deoxy-α-D-gluco-hept-2-ulopyranosonate 
• 848034-55-9 tert-butyl 2,6-anhydro-3,4,5,7-tetra-O-benzoyl-D-glycero-D-gulo-heptonate 
• 848034-82-2 methyl 2-azido-3,4,5,7-tetra-O-benzoyl-2-deoxy-β-D-gluco-hept-2-ulopyranosonate 
• 848034-68-4 tert-butyl 3,4,5,7-tetra-O-benzoyl-2-bromo-2-deoxy-α-D-gluco-hept-2-ulopyranosonate 
• 848034-59-3 2,2,2-trichloroethyl 2,6-anhydro-3,4,5,7-tetra-O-benzoyl-D-glycero-D-gulo-heptonate 
• 848034-80-0 N-(3,4,5,7-tetra-O-benzoyl-2-bromo-2-deoxy-α-D-gluco-hept-2-ulopyranosonoyl)glycine methyl ester 
• 848034-61-7 pentachlorophenyl 2,6-anhydro-3,4,5,7-tetra-O-benzoyl-D-glycero-D-gulo-heptonate 
• 848034-73-1 pentachlorophenyl 3,4,5,7-tetra-O-benzoyl-2-bromo-2-deoxy-α-D-gluco-hept-2-ulopyranosonate 
• 227458-60-8 (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-2-hydroxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione 
• 286369-08-2 (2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-2-benzoyloxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione 
• 6920-09-8 N,N'-di-β,β-2,3,4,6-octa-O-acetyl-D-glucopyranosyl urea 

Relevant articles and documents

C-Glycosyl 1,2,4-triazoles: Synthesis of the 3-β-D-glucopyranosyl-1,5-disubstituted and 5-β-D-glucopyranosyl-1,3-disubstituted variants

Highly variable synthetic routes were elaborated toward trisubstituted C-glycopyranosyl 1,2,4-triazoles. N-Acyl-thioamide derivatives were obtained by acylation of O-perbenzoylated 2,6-anhydro-D-glycero-D-gulo-heptonothioamide by acid chlorides and of thioamides by O-perbenzoylated 2,6-anhydro-D-glycero-D-gulo-heptonoyl chloride. These precursors reacted with substituted hydrazines in a regioselective manner to yield 3-β-D-glucopyranosyl-1,5-disubstituted- and 5-β-D-glucopyranosyl-1,3-disubstituted-1,2,4-triazoles, respectively. Analogous N-acyl-2,6-anhydro-heptonamides failed to give the above triazoles with hydrazines. O-Deprotection of the C-glucosyl 1,2,4-triazoles by the Zemplén method furnished test compounds which showed no inhibition against rabbit muscle glycogen phosphorylase b.

Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media

[RuCl2(DMSO)4] in the presence of N-benzylated 1,3,5-triaza-7-phosphaadamantane efficiently catalyzed the hydration of glycosyl cyanides to the corresponding formamide derivatives in water or water-N-methylpyrrolidone solvent mixture

Synthesis of substituted 2-(β-d-glucopyranosyl)-benzimidazoles and their evaluation as inhibitors of glycogen phosphorylase

Microwave assisted condensation of O-perbenzoylated C-(β-d- glucopyranosyl)formic acid with 1,2-diaminobenzenes in the presence of triphenylphosphite gave the corresponding O-protected 2-(β-d- glucopyranosyl)-benzimidazoles in moderate yields. O-Perbenzoy

Gram-scale synthesis of a glucopyranosylidene-spiro-thiohydantoin and its effect on hepatic glycogen metabolism studied in vitro and in vivo

A high yielding, simple synthesis is described starting from D-glucose to produce gram quantities of a glucopyranosylidene-spiro-thiohydantoin. This compound efficiently inhibited the activity of rat liver glycogen phosphorylase a; moreover, it also activated phosphorylase phosphatase which, in turn, decreased the amount of glycogen phosphorylase a. Both effects result in the inhibition of glycogen mobilization and the formation of glucose from glycogen. Copyright (C) 2000 Elsevier Science Ltd.

A new, scalable preparation of a glucopyranosylidene-spiro- thiohydantoin: One of the best inhibitors of glycogen phosphorylases

Benzobromo-glucose was converted into per-O-benzoylated β-D- glucopyranosyl cyanide by mercury(II) cyanide in nitromethane. Partial hydrolysis of the nitrile with hydrogen bromide in acetic acid gave per-O- benzoylated C-(β-D-glucopyranosyl)formamide. Photobromination using bromine in carbon tetrachloride, chloroform, or dichloromethane gave the corresponding per-O-benzoylated 1-bromo-1-deoxy-β-D-glucopyranosyl cyanide and C-(1-bromo-1-deoxy-β-D-glucopyranosyl)formamide. Reaction of the latter with ammonium thiocyanate in nitromethane gave the per-O-benzoylated C-6S configured glucopyranosylidene-spiro-thiohydantoin together with a small amount of the per-O-benzoylated C-(1-hydroxy-β-D-glucopyranosyl)formamide. Debenzoylation of the spiro-thiohydantoin with sodium methoxide in methanol gave gram amounts of the title inhibitor. The described sequence should be suitable for scaling up and the target compound can be prepared in ~30% overall yield starting from D-glucose. (C) 2000 Elsevier Science Ltd.