75336-82-2

Usage

Uses

Used in Organic Synthesis:
Methyl 3-O-benzyl-a-L-rhamnopyranoside is used as a building block in organic synthesis for the preparation of various rhamnose-derived molecules. Its unique structure allows for the creation of complex organic compounds with potential applications in various industries.
Used in Chemical Research:
Methyl 3-O-benzyl-a-L-rhamnopyranoside is used as a valuable chemical tool in chemical research to study the role of rhamnose in various biological and chemical processes. This helps researchers gain a better understanding of the compound's properties and potential applications.
Used in Food Industry:
Methyl 3-O-benzyl-a-L-rhamnopyranoside is used in the food industry for its ability to modulate biological processes and enhance the properties of certain products. Its unique structure and properties make it a promising ingredient for improving the quality and functionality of food products.
Used in Pharmaceutical Industry:
Methyl 3-O-benzyl-a-L-rhamnopyranoside is used in the pharmaceutical industry due to its potential applications in modulating biological processes. Its unique structure and properties make it a promising candidate for the development of new drugs and therapeutic agents.

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 
• 65475-56-1 methyl 4-O-acetyl-exo-2,3-O-benzylidene-α-L-rhamnopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 

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

Relevant academic research and scientific papers

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-

RADIOLABELED SUGARS FOR IMAGING OF FUNGAL INFECTIONS

Disclosed herein are compounds having a structure according to Formula I and optionally Formula IV. Formula I Formula IV. The compounds may be radiolabeled compounds useful for diagnosis and/or imaging fungal infections. In such embodiments, at least one substituent is a radionuclide, such as 18F. Also disclosed are precursor compounds according to Formula I and/or IV that are useful for making the radiolabeled compounds. In such embodiments, the precursor compound comprises at least one leaving group suitable for introducing a radionuclide, such as 18F, at a desired position. Also disclosed are methods for making and using the compounds, including embodiments of a method for imaging and/or diagnosing a fungal infection in a subject.

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.

Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system

In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.

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.

Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivative

Regioselective, catalyst-controlled monoalkylations of cis-vicinal diol motifs in carbohydrate derivatives, using a diphenylborinic ester precatalyst, are described. Selective installation of benzyl, naphthylmethyl, 4-bromobenzyl and benzyloxymethyl protective groups at a single secondary hydroxy group of ten representative carbohydrate derivatives illustrates the scope of this method. This new mode of catalytic reactivity represents an operationally simple method to access useful monoalkylated building blocks while avoiding the use of stoichiometric quantities of organotin reagents.

Selective 3-O-allylation and 3-O-benzylation of methyl α-D-manno-, α-L-rhamno- and β-L-fuco-pyranoside

The selective 3-O-allylation or 3-O-benzylation of methyl glycosides is a very useful procedure in anhydro sugar synthesis and oligosaccharide synthesis, because it can substantially simplify the reaction pathways. The 'direct stannylation method'3, by which unprotected glycopyranosides were treated with dibutyltin oxide and then alkylated, was effective for the 3-O-allylation of methyl α- (ref. 1) and β-D-galactopyranoside, but 'gave a quantitative recovery of starting material' in the case of methyl α-D-mannopyranoside. We report here a slightly modified procedure for direct stannylation that successfully accomplishes the 3-O-allylation and 3-O-benzylation of methyl α-D-manno-, α-L-rhamno- and β-L-fuco-pyranoside.