73395-15-0

Basic information

• Product Name: methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside
• Synonyms: methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside
• CAS NO: 73395-15-0
• Molecular Weight: 370.402
• Mol File: 73395-15-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside(73395-15-0)
• EPA Substance Registry System: methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside(73395-15-0)

Safety Data

• Hazardous Substances Data: 73395-15-0(Hazardous Substances Data)

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 22277-65-2 Methyl mannoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 774-48-1 (diethoxymethyl)benzene 

Downstream Products

• 4148-58-7 (4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 63598-31-2 methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 
• 100662-84-8 methyl α-D-mannopyranoside 2-benzyl ether 
• 15038-71-8 methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 86342-20-3 methyl 2,6-di-O-benzyl-β-D-mannopyranoside 
• 86342-19-0 methyl 2,4-di-O-benzyl-β-D-mannopyranoside 
• 57783-73-0 methyl 3,4-di-O-benzyl-β-D-mannopyranoside 
• 502181-63-7 methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 502181-59-1 methyl (2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 80738-49-4 methyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranoside 
• 80738-50-7 1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose 

Relevant articles and documents

Rapid assembly of gp120 oligosaccharide moieties via one-pot glycosidation-deprotection sequences

Mannosyl trihaloacetimidate donors equipped with a 2-O-Fmoc group can be effectively activated by catalytic Bi(OTf)3 in glycosidations. Despite the expected participating effect of the Fmoc group, the reaction solvent was found to be decisive f

Total synthesis of the Glc3Man N-glycan tetrasaccharide

The total synthesis of the tetrasaccharide Glcα(1→2)Glcα(1→3)Glcα(1→3)ManαOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide.

The Selective Monobenzylidenation of Some Monosaccharides and Their Derivatives with α,α-Dimethoxytoluene

The treatment of some monosaccharides and their derivatives with α,α-dimethoxytoluene and an acid catalyst in dimethylformamide at about 80 deg C can lead to selective benzylidenation, e.g. methyl α-D-mannopyranoside gives mainly methyl 4,6-O-benzylidene-α-D-mannoside, together with two other minor monobenzylidene derivatives (2,3-) and two minor dibenzylidene derivatives (2,3:4,6-).The treatment of various other pyranoses and pyranosides is also described.As well, a 1H n.m.r. study of the acid transformation of some of the above α-D-mannosides is reported, together with a single-crystal X-ray diffraction structure determination of a novel monobenzylidene derivative, namely methyl (S)-2,3-O-benzylidene-α-D-mannopyranoside.