34820-00-3

Basic information

• Product Name: methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside
• Synonyms: methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside
• CAS NO: 34820-00-3
• Molecular Weight: 610.617
• Mol File: 34820-00-3.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside(34820-00-3)
• EPA Substance Registry System: methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside(34820-00-3)

Safety Data

• Hazardous Substances Data: 34820-00-3(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 67-56-1 methanol 
• 97-30-3 methyl D-galactopyranoside 
• 569329-23-3 Ectyoceramide hexaacetate 
• 571194-37-1 Ectyoceramide 
• 65236-82-0 1,2-O-(α-methoxybenzylidene)-3,4,6-tri-O-benzoyl-β-D-mannopyranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 1391727-72-2 pent-4-enyl 3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 51023-63-3 methyl-α,β-D-mannopyranoside 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside 
• 34234-44-1 methyl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 53182-61-9 methyl 2,3,4-tri-O-benzoyl-β-D-galactopyranoside 
• 1263311-56-3 methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranoside 
• 3396-68-7 methyl 2,3,6-tri-O-benzoyl-α-D-mannopyranoside 
• 80245-08-5 methyl 3,4,6-tri-O-benzoyl-α-D-mannopyranoside 
• 14315-85-6 methyl 3, 6-di-O-benzoyl-α-D-mannopyranoside 

Relevant articles and documents

A carbohydrate-anion recognition system in aprotic solvents

A carbohydrate-anion recognition system in nonpolar solvents is reported, in which complexes form at the B-faces of β-D-pyranosides with H1-, H3-, and H5-cis patterns similar to carbohydrate-π interactions. The complexation effect was evaluated for a range of carbohydrate structures; it resulted in either 1:1 carbohydrate-anion complexes, or 1:2 complex formation depending on the protection pattern of the carbohydrate. The interaction was also evaluated with different anions and solvents. In both cases it resulted in significant binding differences. The results indicate that complexation originates from van der Waals interactions or weak CHA- hydrogen bonds between the binding partners and is related to electron-withdrawing groups of the carbohydrates as well as increased hydrogen-bond-accepting capability of the anions. Facial recognition: A carbohydrate-anion recognition system is reported, in which complexes form at the B-faces of β-D-pyranosides with H1-, H3-, and H5-cis patterns similar to carbohydrate-π interactions (see scheme). The interaction was also evaluated with different anions and solvents. In both cases it resulted in significant binding differences.

Methyl 1,2-orthoesters as useful glycosyl donors in glycosylation reactions: A comparison with n-pent-4-enyl 1,2-orthoesters

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors - upon BF3·Et 2O activation in CH2Cl2 - in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2-orthoesters can be also used in regioselective glycosylation protocols with monosaccharide diols, in which they display good regioselectivity. Copyright

Unexpected stereocontrolled access to 1α,1′β-disaccharides from methyl 1,2-ortho esters

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1α,1′β-disaccharides, upon treatment with BF 3?Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.