101312-02-1

Basic information

• Product Name: methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside
• Synonyms: methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside
• CAS NO: 101312-02-1
• Molecular Weight: 462.543
• Mol File: 101312-02-1.mol
• Article Data: 91

Chemical Properties

• CAS DataBase Reference: methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside(101312-02-1)
• EPA Substance Registry System: methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside(101312-02-1)

Safety Data

• Hazardous Substances Data: 101312-02-1(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 1000813-65-9 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 220645-86-3 p-methylphenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 28244-94-2 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 850416-39-6 p-methylphenyl 2,3-di-O-benzyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside 
• 942043-17-6 4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 56-23-5 tetrachloromethane 

Downstream Products

• 51842-32-1 methyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-galacto-pyranoside 
• 56750-58-4 methyl 6-deoxy-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside 
• 67381-20-8 methyl 2,3-di-O-benzyl-6-deoxy-α-D-xylo-hexopyranosid-4-ulose 
• 13231-29-3 methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranoside 
• 14532-80-0 methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-galactopyranoside 
• 51642-43-4 1,2,3,4-Tetra-O-acetyl-6-azido-6-desoxy-α-D-glucopyranose 
• 19488-48-3 methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 68622-25-3 Methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside 
• 13231-27-1 Methyl-2,3-di-O-benzyl-6-desoxy-α-D-galactopyranosid 
• 98807-61-5 1-O-methyl-2,3,6-tri-O-benzyl-4-keto-α-D-glucopyranoside 
• 54522-57-5 methyl-2,3-di-O-benzyl-6-O-(4-toluenesulfonyl)-α-D-glucopyranoside 
• 88713-85-3 methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside 
• 54522-58-6 methyl 6-azido-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside 
• 674782-48-0 methyl 4,6-diazido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranoside 

Relevant articles and documents

Intramolecular OH×××FC hydrogen bonding in fluorinated carbohydrates: CHF is a better hydrogen bond acceptor than CF2

An intramolecular bifurcated H-bond from the axial HO-2 group to the axial F-4 atom and to the O5 atom of α-D-hexopyranosides in apolar solvents is evidenced in 1H NMR spectra. The H-accepting properties of the F atom are modulated by the orien

Chemistry of 4,6-O-benzylidene-D-glycopyranosyl triflates: Contrasting behavior between the gluco and manno series

Activation of either anomer of S-phenyl 2,3-di-O-benzyl-4,6-O- benzylidene-1-deoxy-1-thia-D-glucopyranoside with triflic anhydride in dichloromethane at -78 °C in the presence of 2,6-di-tert-butyl-4- methylpyridine affords a highly active glycosylating species which, on addition of alcohols, provides α-glucosides with high selectivity. This selectivity stands in stark contrast to the analogous mannopyranoside series, which affords the β-mannosides with excellent selectivity under the same conditions. Low-temperature NMR experiments support the notion that a glucosyl triflate is formed in the initial activation step. Possible reasons for the diverging stereoselectivity in the gluco and manno series are discussed.

Electrosyntheses of disaccharides from phenyl or ethyl 1-thioglycosides

Constant current electrolyses of the glycosyl donors phenyl and ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside in dry acetonitrile in the presence of various primary and secondary sugar alcohols, performed in an undivided cell, gave β-linked disaccharide derivatives selectively in good yields.Phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside gave the β-glucosides exclusively in good to moderate yields.

Synthesis of a pentasaccharide repeating unit of the extracellular polysaccharide produced by Lactobacillus delbrueckii subsp. bulgaricus 291

A pentasaccharide methyl glycoside has been synthesized efficiently using a modified glycosylation strategy. This pentasaccharide is a repeating unit of the exopolysaccharides produced by Lactobacillus delbrueckii subsp. bulgaricus 291.

Stereoselective β-mannosylation via anomeric O-Alkylation: Concise synthesis of β-D-Xyl-(l→2)-β-D-Man-(1→4)-α-D-Glc-OMe, a trisaccharide oligomer of the hyriopsis schlegelii glycosphingolipid

Synthesis of ?-D-Xyl-(l→2)-?-D-Man-(1→4)-α-D-Glc-OMe (1), a trisaccharide oligomer of the Hyriopsis schlegelii glycosphingolipid is described. The synthesis involves a key ?-mannosylation via cesium carbonate-mediated anomeric O-alkylation for direct synt

Direct and convenient method of regioselective benzylation of methyl α-D-glucopyranoside

A facile and convenient method for the direct preparation of methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside (2) by the regioselective benzylation of methyl α-D-glucopyranoside (1) with benzyl bromide in the presence of mild bases K2CO3 and KOH (1:1) withou

Synthesis of β-Mannopyranosides from α-Epimers by Radical Inversion. 1,6-Hydrogen Transfer Reactions of 2-O-(2-Bromoaryl)dimethylsilyl-α-methyl-D-mannopyranosides

Intramolecular hydrogen transfer reactions of 3-O-acyl-α-methyl-D-mannopyranosides occur in a 1,6-fashion to give inverted β-mannopyranosides.The yields are limited by competing 1,5-hydrogen transfer reactions that give isomeric α-glucopyranosides.

How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?

The reaction of glycosyl donor phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with NIS/TfOH(cat.) was systematically studied under various reaction conditions. Neither the molecular sieve pore size nor amount of NIS activator was found to have a

Substrate Substitution in Kanosamine Biosynthesis Using Phosphonates and Phosphite Rescue

Kanosamine is an antibiotic and antifungal compound synthesized from glucose 6-phosphate (G6P) inBacillus subtilisby the action of three enzymes: NtdC, which catalyzes NAD-dependent oxidation of the C3-hydroxyl; NtdA, a PLP-dependent aminotransferase; and