37797-55-0

Basic information

• Product Name: phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• CAS NO: 37797-55-0
• Molecular Weight: 424.405
• Mol File: 37797-55-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside(37797-55-0)
• EPA Substance Registry System: phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside(37797-55-0)

Safety Data

• Hazardous Substances Data: 37797-55-0(Hazardous Substances Data)

Upstream product

• 108-95-2 phenol 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 604-70-6 methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 3262-89-3 triphenylboroxine 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 98-80-6 phenylboronic acid 
• 19186-39-1 1,2,3,4,6-penta-O-acetyl-α-D-galactopyranose 
• 287967-74-2 (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1095-03-0 triphenylborane 

Downstream Products

• 898815-55-9 phenyl-α-D-talopyranoside 
• 1464-44-4 phenyl α-D-mannoopyranoside 
• 15548-42-2 phenyl β-D-mannopyranoside 

Relevant articles and documents

Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature

Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.

Phenyl glycosides – Solid-state NMR, X-ray diffraction and conformational analysis using genetic algorithm

The X-ray structures of 2,6-dimethylphenyl and phenyl 2,3,4,6-tetra-O-acetyl β-glucosides (1 and 3) and phenyl α-mannoside (6) were obtained. The independent part of the unit cell of the glycosides 1 and 6 was formed by one molecule, and for the glucoside 3, two molecules in the crystal cell were observed. In deacetylated glycosides 4 and 6 the crystal structure was established by a hydrogen bond network formed between the sugar hydroxyls and solvent molecules. The 13C CPMAS NMR spectra of aryl glycosides 1–6 were analysed. In the spectrum of 3, doubling of the C4 aryl signal was observed which confirmed the presence of two independent molecules in the solid sample. The GAAGS (Genetic Algorithm-Assisted Grid Search) method was used to determine the low-energy conformers of α-mannosides and β-glucosides. The orientation of the aryl pendant group was calculated using Molecular Mechanics (MMFF94) as well as Quantum Mechanics theory (DFT, B3LYP/6-31 + G(d,p)).

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