120498-97-7

Basic information

• Product Name: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside
• Synonyms: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside
• CAS NO: 120498-97-7
• Molecular Weight: 511.485
• Mol File: 120498-97-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside(120498-97-7)
• EPA Substance Registry System: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside(120498-97-7)

Safety Data

• Hazardous Substances Data: 120498-97-7(Hazardous Substances Data)

Upstream product

• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 108-95-2 phenol 
• 109-63-7 trifluoroborane diethyl ether 
• 17460-45-6 tetra-acetyl glucosamine 

Downstream Products

• 38223-13-1 phenyl-(O²-aza-β-D-glucopyranoside) 
• 13089-21-9 1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose 
• 130539-42-3 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride 

Relevant articles and documents

Hydration of Sugars in the gas phase: Regioselectivity and conformational choice in N-acetyl glucosamine and glucose

The influence of an acetamido group in directing the preferred choice of hydration sites in glucosamine and a consequent extension of the working rules governing regioselective hydration and conformational choice, have been revealed through comparisons between the conformations and structures of "free" and multiply hydrated phenyl N-acetyl-β-D-glucosamine (sβpGlcNAc) and phenyl β-D-glucopyranoside (βpGlc), isolated in the gas phase at low temperatures. The structures have been assigned through infrared ion depletion spectroscopy conducted in a supersonic jet expansion, coupled with computational methods. The acetamido motif provides a hydration focus that overwhelms the directing role of the hydroxymethyl group; in multiply hydrated βpGlcNAc the water molecules are all located around the acetamido motif, on the "axial" faces of the pyranose ring rather than around its edge, despite the equatorial disposition of all the hydrophilic groups in the ring. The striking and unprecedented role of the C-2 acetamido group in controlling hydration structures may, in part, explain the differing and widespread roles of GlcNAc, and perhaps GalNAc, in nature.

Preparation of glucosaminyl muramic acid derivatives

The present invention provides a method for the preparation of disaccharides, such as glucosaminyl muramic acids peptides and derivatives. The method includes condensing a protected muramic acid ester with a 1-organothio- or 1-fluoroglucosamine derivative in the presence of a suitable promoter to produce a protected glucosaminyl muramic acid ester. The protected glucosaminyl muramic acid ester may be used to prepare disaccharide peptides, such as N-acetylglucosaminyl-N-acetylmuramyl dipeptides, which have demonstrated immunological activity. Protected muramic acid esters and 1-organothio- or 1-fluoro- glucosamine compounds which may be employed as intermediates in the method are also provided.