55628-55-2

Basic information

• Product Name: 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-α-D-glucopyranoside
• Synonyms: 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-α-D-glucopyranoside
• CAS NO: 55628-55-2
• Molecular Weight: 490.596
• Mol File: 55628-55-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-α-D-glucopyranoside(55628-55-2)
• EPA Substance Registry System: 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-α-D-glucopyranoside(55628-55-2)

Safety Data

• Hazardous Substances Data: 55628-55-2(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 32365-83-6 1,2-O-isopropylidene-α-D-glucopyranosae 
• 136305-64-1 methyl 4,5,7-tri-O-benzyl-2,3-O-isopropylidene-α-D-gluco-hept-2-ulopyranosonate 
• 136305-59-4 methyl 4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate 
• 127994-68-7 methyl onate 
• 110390-66-4 methyl (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-5,6-dihydro-4H-pyran-2-carboxylate 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 77-76-9 2,2-dimethoxy-propane 
• 677301-12-1 1-(E)-3,4,6-tri-O-benzyl-1,2-dideoxy-1-methylthio-D-arabino-hex-1-enitol 
• 67-64-1 acetone 
• 100-39-0 benzyl bromide 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 

Downstream Products

• 162843-28-9 benzyl 3,4,6-tri-O-benzyl-2-O-(2-hydroxyethyl)-α-D-glucopyranoside 
• 2280-43-5 O²-(2-hydroxy-ethyl)-D-glucose 
• 120269-17-2 Benzyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 40246-26-2 3,4,6-tri-O-benzyl-α-D-glucopyranose 

Relevant articles and documents

Preparation method of tribenoside

The invention discloses a preparation method of tribenoside. The method comprises the following steps: adding monoacetone glucose and a phase transfer catalyst to benzyl chloride, controlling the reaction temperature of a system, adding an inorganic base solution dropwise to obtain a crude product of tribenzyl monoacetone glucose, performing three-stage molecular distillation for purification toobtain high-purity tribenzyl monoacetone glucose, and adding high-purity tribenzyl monoacetone glucose to ethanol hydrochloride to prepare tribenoside. The method has the advantages of simple and efficient synthesis process, reasonable process, high synthesis efficiency and high yield; reaction operation is simple and convenient, tribenoside contains fewer impurities and is higher in purity and content, operation is convenient, and the European pharmacopoeia standards can be met directly.

One-pot conversion of glycals to cis-1,2-isopropylidene-α-glycosides

Described is a general method for the conversion of glycals to the corresponding 1,2-cis-isopropylidene-α-glycosides. Epoxidation of glycals with dimethyldioxirane followed by ZnCl2-catalyzed addition of acetone converted a variety of protected glycals into 1,2-cis-isopropylidene-α-glycosides in good yield. The reaction is compatible with a range of protecting groups, including esters, benzyl ethers, and silyl ethers, as well as free hydroxyl groups. This method has been applied to develop a synthesis of protected glucuronic acid 1, a key intermediate in the synthesis of glycosaminoglycans. Compound 1 was produced in seven steps and 32% overall yield.

Preparation of O-Hydroxyethyl and O-Hydroxypropyl Derivatives of D-Glucose and 2-Acetamido-2-deoxy-D-glucose for Studies of Modified Hyaluronic Acid

Some hydroxyethyl and hydroxypropyl derivatives of D-glucose and of 2-acetamido-2-deoxy-D-glucose have been sunthesized for use as reference substances for structural studies of hydroxyethylated and hydroxypropylated hyaluronic acid.Hydroxyethyl and hydroxypropyl substituents were introduced in the 2-O- or 3-O-position of D-glucose and in the 4-O- or 6-O-positions of 2-acetamido-2-deoxy-D-glucose by reaction of suitably protected sugars with either ethylene oxide or propylene oxide.For hydroxyethyl derivatives yields varied between 21 and 74percent and with a substantial portion of the doubly alkylated compounds.For hydroxypropyl derivatives yields varied between 15 and 80percent.Only trace amounts of the doubly alkylated compounds were found.The proportions of the respective derivatives were estimated using GLC-MS.All products were characterized by 1H and 13C NMR spectroscopy.