75336-82-2

Basic information

• Product Name: Methyl 3-O-benzyl-a-L-rhamnopyranoside
• Synonyms: Methyl 3-O-benzyl-a-L-rhamnopyranoside;Methyl 3-O-benzyl-alpha-L-rhamnopyranoside;Methyl 3-O-benzyl-α-L-rhaMnopyranoside
• CAS NO: 75336-82-2
• Molecular Formula: C₁₄H₂₀O₅
• Molecular Weight: 268.3056
• Mol File: 75336-82-2.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 3-O-benzyl-a-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-O-benzyl-a-L-rhamnopyranoside(75336-82-2)
• EPA Substance Registry System: Methyl 3-O-benzyl-a-L-rhamnopyranoside(75336-82-2)

Safety Data

• Hazardous Substances Data: 75336-82-2(Hazardous Substances Data)

Usage

General Description

Methyl 3-O-benzyl-a-L-rhamnopyranoside is a chemical compound that belongs to the family of rhamnose derivatives. It is a methylated form of alpha-L-rhamnose with a benzyl moiety attached to the 3-O position. Methyl 3-O-benzyl-a-L-rhamnopyranoside is commonly used in organic synthesis and chemical research as a building block for the preparation of various rhamnose-derived molecules. It possesses potential applications in the food and pharmaceutical industries due to its ability to modulate biological processes and enhance the properties of certain products. Methyl 3-O-benzyl-a-L-rhamnopyranoside is a valuable chemical tool for studying the role of rhamnose in various biological and chemical processes.

Upstream product

• 100-39-0 benzyl bromide 
• 1128-40-1 methyl L-rhamnopyranoside 
• 65529-46-6 Methyl exo-2,3-di-O-benzylidene-α-L-rhamnopyranoside 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 65475-56-1 methyl 4-O-acetyl-exo-2,3-O-benzylidene-α-L-rhamnopyranoside 

Downstream Products

• 89202-43-7 methyl 2,4-di-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside 
• 65529-46-6 Methyl exo-2,3-di-O-benzylidene-α-L-rhamnopyranoside 
• 940274-17-9 methyl 2-O-acetyl-3-O-benzyl-α-L-rhamnopyranoside 
• 88331-96-8 methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 139760-16-0 Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside 
• 139760-05-7 Methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 139760-06-8 O-(2,3,4-Tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl chloride 
• 139869-57-1 C₅₉H₅₇ClO₂₁ 
• 139760-15-9 Methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside 
• 139760-12-6 C₆₁H₆₀O₂₃ 
• 75336-79-7 methyl 2,3-di-O-benzyl-α-L-rhamnopyranoside 
• 76520-79-1 methyl 4-O-acetyl-2,3-di-O-benzyl-α-L-rhamnopyranoside 

Relevant articles and documents

Scalable Sn-Catalyzed Regioselective Allylation of 1-Methyl- l -α-rhamnopyranoside

A robust selective allylation of 1-methyl-l-α-rhamnose was developed using di-n-butyltin oxide (n-Bu2SnO) as the catalyst. Proton sponge was found to be the optimal base for high regioselective control. The optimized condition afforded the 3-O-

Benzoxaborole Catalyst for Site-Selective Modification of Polyols

The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.

9-Hetero-10-boraanthracene-derived borinic acid catalysts for regioselective activation of polyols

Heteraborinine-derived borinic acids serve as efficient catalysts for regioselective monofunctionalization of di- and polyols. Arylborinic acids of this type, wherein the B-OH group is incorporated into a 6π electron system, display both improved catalytic activity for functionalization of diols and enhanced stability towards air oxidation relative to the 'parent' diphenylborinic acid (Ph2BOH). These properties enable their applications at loadings as low as 0.1 mol% and without the need for a stabilizing precatalyst ligand (e.g., ethanolamine). Complexation studies, computation and kinetic data suggest that while the heteraborinine-derived borinic acids show significantly lower association constants with substrates than Ph2BOH, this effect is more than compensated for by the increased nucleophilicity of their tetracoordinate diol adducts.