286369-05-9

Basic information

• Product Name: 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosylcyanide
• Synonyms: 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosylcyanide
• CAS NO: 286369-05-9
• Molecular Formula: C₃₅H₂₇NO₉
• Molecular Weight: 605.59
• Mol File: 286369-05-9.mol

Chemical Properties

• Boiling Point: 764.7±60.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosylcyanide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosylcyanide(286369-05-9)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosylcyanide(286369-05-9)

Safety Data

• Hazardous Substances Data: 286369-05-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry Research:
2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosylcyanide is used as a research compound for the study of carbohydrate chemistry and biochemistry. Its complex structure and reactivity make it a valuable tool for understanding the properties and interactions of glucose derivatives.
Used in Synthesis of Other Organic Compounds:
2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosylcyanide is used as a building block in the synthesis of more complex molecules. Its unique properties and reactivity allow for the creation of a wide range of organic compounds, making it an important component in the field of organic chemistry.
Used in Chemical Reactions:
2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosylcyanide is used as a reagent in various chemical reactions. Its complex structure and reactivity make it a versatile component that can be used to facilitate a range of chemical processes and transformations.

Upstream product

• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 592-04-1 mercury(II) cyanide 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 100-52-7 benzaldehyde 
• 98-88-4 benzoyl chloride 
• 286369-06-0 2,6-anhydro-3,4,5,7-tetra-O-benzoyl-D-glycero-D-gulo-heptonamide 
• 879-18-5 naphthalene-1-carbonic acid chloride 
• 358738-50-8 C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)thioformamide 

Downstream Products

• 286369-06-0 2,6-anhydro-3,4,5,7-tetra-O-benzoyl-D-glycero-D-gulo-heptonamide 
• 262849-67-2 2,3,4,6-tetra-O-benzoyl-1-bromo-1-deoxy-β-D-glucopyranosyl cyanide 
• 358738-50-8 C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)thioformamide 
• 595580-15-7 C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formaldehyde semicarbazone 
• 352310-77-1 3,4,5,7-tetra-O-benzoyl-2,6-anhydro-D-glycero-D-gulo-heptose tosylhydrazone 
• 915396-24-6 C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidoxime 
• 358738-57-5 3,5-bis(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-thiadiazole 
• 1320161-33-8 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-ethynyl-1,3,4-oxadiazole 
• 1320161-42-9 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-chloromethyl-1,3,4-oxadiazole 
• 1320161-43-0 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-azidomethyl-1,3,4-oxadiazole 
• 1320161-48-5 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-(1-phenyl-1,2,3-triazol-4-yl)-1,3,4-oxadiazole 
• 1320161-49-6 C₄₈H₃₅N₅O₁₀ 
• 1320161-51-0 C₄₈H₃₅N₅O₁₀ 
• 1320161-53-2 C₅₂H₄₇N₅O₁₉ 

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.

Synthesis of 5-aryl-3-C-glycosyl- and unsymmetrical 3,5-diaryl-1,2,4-triazoles from alkylidene-amidrazones

Among 1,2,4-triazole derivatives with versatile biological activities 3-C-glucopyranosyl-5-substituted-1,2,4-triazoles belong to the most efficient inhibitors of glycogen phosphorylase, and are thus potential antidiabetic agents. In seeking new synthetic methods for this class of compounds oxidative ring closures of N1-alkylidene carboxamidrazones were studied. O-Peracylated N1-(β-d-glycopyranosylmethylidene)-arenecarboxamidrazones were prepared from the corresponding glycosyl cyanides and amidrazones by Raney-Ni reduction in the presence of NaH2PO2. Bromination of the so obtained compounds by NBS gave hydrazonoyl bromide type derivatives which were ring closed to 3-C-glycosyl-5-substituted-1,2,4-triazoles in pyridine or by NH4OAc in AcOH. Under the same conditions O-perbenzoylated N1-arylidene-C-(β-d-glucopyranosyl)-formamidrazones gave the expected 1,2,4-triazoles as minor products only. N1-Arylidene-arenecarboxamidrazones were also transformed into 3,5-diaryl-1,2,4-triazoles with NBS/NH4OAc in AcOH indicating high functional group tolerance and general applicability of the method.

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.

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.