102816-25-1

Basic information

• Product Name: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl azide
• Synonyms: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl azide
• CAS NO: 102816-25-1
• Molecular Weight: 460.4
• Mol File: 102816-25-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl azide(102816-25-1)
• EPA Substance Registry System: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl azide(102816-25-1)

Safety Data

• Hazardous Substances Data: 102816-25-1(Hazardous Substances Data)

Usage

General Description

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl azide is a chemical compound that is primarily used in organic chemistry research and in the field of carbohydrate chemistry. It is an azide derivative of a glucopyranosyl sugar, and is often employed as a reagent for the modification of carbohydrates and glycoconjugates. The molecule contains acetyl and phthalimido groups, which are commonly used for protecting the hydroxyl groups on the sugar to allow for selective chemical reactions. As an azide derivative, it is also capable of participating in azide-alkyne cycloaddition reactions, which are widely used in the synthesis of complex organic molecules. Overall, this compound is a valuable tool for the chemical modification and functionalization of carbohydrates in the laboratory setting.

Upstream product

• 10028-45-2 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 
• 70831-94-6 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-phthalimido-2-deoxy-α-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 85-44-9 phthalic anhydride 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 

Downstream Products

• 1361486-00-1 1-(2'-deoxy-2'-phthalimido-3',4',6'-tri-O-acetyl-α-D-glucopyranosyl)-4-phenyl-1,2,3-triazole 

Relevant articles and documents

UDP-GlcNAc Analogues as Inhibitors of O-GlcNAc Transferase (OGT): Spectroscopic, Computational, and Biological Studies

A series of glycomimetics of UDP-GlcNAc, in which the β-phosphate has been replaced by either an alkyl chain or a triazolyl ring and the sugar moiety has been replaced by a pyrrolidine ring, has been synthesized by the application of different click-chemistry procedures. Their affinities for human O-GlcNAc transferase (hOGT) have been evaluated and studied both spectroscopically and computationally. The binding epitopes of the best ligands have been determined in solution by means of saturation transfer difference (STD) NMR spectroscopy. Experimental, spectroscopic, and computational results are in agreement, pointing out the essential role of the binding of β-phosphate. We have found that the loss of interactions from the β-phosphate can be counterbalanced by the presence of hydrophobic groups at a pyrroline ring acting as a surrogate of the carbohydrate unit. Two of the prepared glycomimetics show inhibition at a micromolar level.

A (13)C-N.M.R. INVESTIGATION OF GLYCOSYL AZIDES AND OTHER AZIDO SUGARS: STEREOCHEMICAL INFLUENCES ON THE ONE-BOND (13)C-(1)H COUPLING CONSTANTS

Unambigous (13)C assignments have been obtained, using 2D-n.m.r. techniques, for several glycosyl azides, 6-deoxyglucosyl azides, 2-acylamino-2-deoxyglycosyl azide, and some 2- and 3-azido monosaccharide derivatives.For non-anomeric C-H-bonds the 1JC,Heq. values are 4-9 Hz larger than the 1JC,Hαx. values.A substituent (hydroxyl, acetoxyl, alkoxyl, azido, etc.) in 1,3-diaxial relationship with Hax. significantly increases the value of 1JC,Hαx..Bond-angle distortions in the fused-ring bicyclic systems of some isopropylidene derivatives result in 1JC,Hαx. values being larger than 1JC,Heq. values.Electronic and stericeffects of substituents at non-anomeric carbons may alter the 1JC,H values for anomeric carbons to such an extent that they may no longer be useful for diagnosing anomeric configuration.Bond-angle deformations also influence the (13)C chemical shift differences in α- and β-anomers at C-5 and, to a lesser extent, at C-3.