6988-40-5

Basic information

• Product Name: methyl 2,3-di-O-benzyl-α-D-mannopyranoside
• CAS NO: 6988-40-5
• Molecular Weight: 374.434
• Mol File: 6988-40-5.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: methyl 2,3-di-O-benzyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-benzyl-α-D-mannopyranoside(6988-40-5)
• EPA Substance Registry System: methyl 2,3-di-O-benzyl-α-D-mannopyranoside(6988-40-5)

Safety Data

• Hazardous Substances Data: 6988-40-5(Hazardous Substances Data)

Upstream product

• 13035-24-0 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 64-19-7 acetic acid 
• 101312-02-1 methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 71117-37-8 (2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 23392-28-1 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 1092482-98-8 2,3-di-O-benzyl-4-O-(o-nitro)benzyl-α-D-mannopyranoside 
• 1610712-47-4 methyl 4,6-O-(2,6-dimethylbenzylidene)-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 1610712-48-5 methyl 2,3-di-O-benzyl-4,6-(2,6-dimethylbenzylidene)-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 16802-97-4 Methyl 4,6-O-isopropylidene-β-D-glucopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 

Downstream Products

• 118545-11-2 methyl 2,3-di-O-benzyl-4,6-bis-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside 
• 82185-95-3 methyl 2,3-di-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 169396-75-2 (2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol 
• 20786-72-5 methyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranoside 
• 4356-79-0 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 57783-72-9 methyl 2,3,4-tri-O-benzyl-6-O-methyl-α-D-glucopyranoside 
• 82231-37-6 methyl 4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 82231-38-7 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 82231-39-8 methyl 2,3,4-tri-O-benzyl-6-O-methyl-β-D-glucopyranoside 
• 5155-50-0 Methyl-(6-O-methyl-β-D-glucopyranosid) 
• 122079-61-2 methyl 2,3-di-O-benzyl-4-O-methanesulfonyl-6-O-propionyl-β-D-galactopyranoside 
• 122079-84-9 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol 

Relevant articles and documents

Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity

The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting-group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis-glucosylations.

A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols

An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment-friendly.

Selective 4,6-O-benzylidene formation of methyl α-d-mannopyranoside using 2,6-dimethylbenzaldehyde

While methyl α-d-glucopyranosides and α-d-galactopyranosides selectively form 4,6-O-benzylidenes when reacted with excess benzaldehyde in the presence of acid catalyst methyl α-d-mannopyranosides does not exhibit the same selectivity because of the cis-ar