37776-15-1

Basic information

• Product Name: 6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose
• Synonyms: 6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose
• CAS NO: 37776-15-1
• Molecular Weight: 414.455
• Mol File: 37776-15-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose(37776-15-1)
• EPA Substance Registry System: 6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose(37776-15-1)

Safety Data

• Hazardous Substances Data: 37776-15-1(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 98-88-4 benzoyl chloride 
• 100-44-7 benzyl chloride 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 

Downstream Products

• 42926-91-0 3-O-benzyl-1,6-anhydro-β-L-idopyranose 
• 334834-19-4 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside 
• 657395-01-2 1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose 
• 657395-02-3 6-O-acetyl-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate 
• 657395-03-4 C₅₅H₅₁Cl₃N₄O₁₃ 
• 657395-07-8 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate 
• 657395-06-7 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl levulinate 
• 657395-04-5 C₇₄H₇₂N₆O₁₈ 
• 42926-89-6 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose 
• 37776-17-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 142657-42-9 tert-butyldimethylsilyl 6-O-benzoyl-3-O-benzyl-α-D-glucopyranoside 
• 142657-26-9 tert-butyldimethylsilyl 6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside 
• 142657-40-7 O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α/β-D-glucopyranoside 
• 142657-31-6 O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 

Relevant articles and documents

Synthesis and antimicrobial activity of (?)-cleistenolide and analogues

Using the “chiral pool” approach, two modified total syntheses of the biologically active δ-lactone cleistenolide (1) have been achieved starting from D-glucose. These approaches also enabled the preparation of novel analogues and derivatives of natural product 1. The applied strategy for the synthesis of 1 involves: the initial degradation of the chiral precursor for a single C-atom, C2-fragment chain extension using Z-selective Wittig reaction, and the final δ-lactonization. All tested cleistenolide analogues displayed antimicrobial activity against a panel of nine microbial strains, most of them superseding the activity of cleistenolide itself, and, in some cases, coming close in value to the observed minimal inhibitory concentrations of chloramphenicol. Increased lipophilicity of the derivatives and the non-sterically congested conjugated lactone moiety were a prerequisite for analogues with high inhibitory activity against S. aureus and, in general, Gram-positive bacteria.

Synthesis of heparin oligosaccharides and their interaction with eosinophil-derived neurotoxin

A convenient route for the synthesis of heparin oligosaccharides involving regioselective protection of d-glucosamine and a concise preparation of rare l-ido sugars from diacetone α-d-glucose is described. Stereoselective coupling of a d-glucosamine-derived trichloroacetimidate with a 1,6-anhydro-β-l-idopyranosyl 4-alcohol gave the desired α-linked disaccharide, which was used as repeating unit for dual chain elongation and termination. Stepwise assembly from the reducing to the non-reducing end with a d-glucosamine-derived monosaccharide as starting unit furnished the oligosaccharide skeletons having different chain lengths. A series of functional group transformations afforded the expected heparin oligosaccharides with 3, 5 and 7 sugar units. Interaction of these oligosaccharides with eosinophil-derived neurotoxin (EDN), a cationic ribonuclease and a mediator produced by human eosinophils, was further investigated. The results revealed that at 5 μg mL-1, the heptasaccharide has sufficiently strong interference to block EDN binding to Beas-2B cells. The tri- and pentasaccharides have moderate inhibitory properties at 50 μg mL-1 concentration, but no inhibition has been observed at 10 μg mL-1. The IC50 values of the tri-, penta- and heptasaccharides are 69.4, 47.2 and 0.225 μg mL-1, respectively.

Synthesis of Heparin Oligosaccharides

An efficient preparation of rare 2-O-benzoyl-3-O-benzyl-1,6-anhydro-β-l-idopyranose from commercially available diacetone α-d-glucose in five straightforward steps is described here. With this key building block in hand, the total syntheses of heparin oligosaccharides with three, five, seven, and nine sugar units are successfully carried out. Copyright