57784-06-2

Basic information

• Product Name: methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside
• Synonyms: methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside
• CAS NO: 57784-06-2
• Molecular Weight: 506.509
• Mol File: 57784-06-2.mol

Chemical Properties

• CAS DataBase Reference: methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside(57784-06-2)
• EPA Substance Registry System: methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside(57784-06-2)

Safety Data

• Hazardous Substances Data: 57784-06-2(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 4137-35-3 methyl 2,3-di-O-benzoyl-α-D-glucopyranoside 
• 10364-94-0 1-benzoylimidazole 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 613-90-1 benzoyl cyanide 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 6748-85-2 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 356060-80-5 methyl 2,3,4-tri-O-benzoyl-6-triisopropylsilyl-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 79580-70-4 Methyl 2,3,6-tri-O-benzoyl-4-O-trifluoromethanesulfonyl-α-D-galactopyranoside 
• 3601-36-3 methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 21056-53-1 methyl O²-benzoyl-α-D-glucoside 
• 92516-59-1 methyl 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-α-D-idopyranoside 

Downstream Products

• 131643-24-8 methyl 4-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-α-D-glycopyranoside 
• 154540-02-0 methyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 57784-05-1 methyl 2,3,6-tri-O-benzoyl-4-O-<(4-bromophenyl)sulfonyl>-α-D-glucopyranoside 
• 149832-00-8 C₃₀H₂₈O₉S₂ 
• 132556-23-1 methyl 2,3,6-tri-O-benzoyl-4-O-methyl-α-D-glucopyranoside 
• 86158-35-2 methyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside 
• 130052-71-0 methyl O-(tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-tri-O-benzoyl-α-D-glucopyranoside 
• 191222-89-6 C₇₄H₆₈O₁₄ 
• 150204-66-3 methyl(2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside 

Relevant articles and documents

4-(tert -Butyldiphenylsilyloxy)-2,2-dimethylbutanoyl: An Easily Removable Pivaloyl-Type Protecting Group with High Orthogonality

Protecting groups play multiple and vital roles during the synthesis of carbohydrates and other natural products. We herein report the installation and orthogonal cleavage, under mild conditions, of a 4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutanoyl (BDMB) group as a sterically hindered pivaloyl-type hydroxy protecting group. The compatibility of this substituent with the removal of other protecting groups is also investigated. Due to its advantageous properties, BDMB is anticipated to function as a valuable agent for masking hydroxy groups.

Introducing Oxo-Phenylacetyl (OPAc) as a Protecting Group for Carbohydrates

A series of oxo-phenylacetyl (OPAc)-protected saccharides, with divergent base sensitivity profiles against benzoyl (Bz) and acetyl (Ac) were synthesized, and KHSO5/AcCl in methanol was identified as an easy, mild, selective, and efficient deprotecting reagent for their removal in the perspective of carbohydrate synthesis. Timely monitoring of AcCl reagent was supportive in both sequential and simultaneous deprotecting of OPAc, Bz, and Ac. The salient feature of our method is the orthogonal stability against different groups, its ease to generate different valuable acceptors using designed monosaccharides, and use of OPAc as a glycosyl donar.

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.

Stereoinversion of Stereocongested Carbocyclic Alcohols via Triflylation and Subsequent Treatment with Aqueous N,N-Dimethylformamide

A convenient method for the stereoinversion of secondary alcohols, applicable to stereocongested carbocyclic substrates, is reported. A simple three-step procedure, including triflylation of the hydroxy group, nucleophilic oxygenative displacement by the treatment with aqueous N,N-dimethylformamide (DMF), and methanolysis, allowed for efficient stereoinversion of various substrates, including sugar derivatives, in one pot.

Regioselective oxidative cleavage of benzylidene acetals of glycopyranosides with periodic acid catalyzed by tetrabutylammonium bromide

A combination of periodic acid, tetrabutylammonium bromide, and wet alumina in dichloromethane efficiently oxidized benzylidene acetals of carbohydrates to the corresponding hydroxybenzoates in excellent yields (>90%). Under these conditions, other protec

Regioselective control in the oxidative cleavage of 4,6-o-benzylidene acetals of glycopyranosides by dimethyldioxirane

"Chemical Equation Presentation" The oxidative cleavage of 4,6-O-benzylidene acetals of glycopyranosides using dimethyldioxirane (DMDO) leads to the corresponding hydroxy-benzoates in excellent yields. With a proper choice of the neighboring protecting groups, this oxidative fragmentation provides the 6- or 4-hydroxyl derivatives in a highly regioselective manner.

Studies on the substrate specificity of Escherichia coli galactokinase

(Martix presented) In vitro glycorandomization (IVG) technology is dependent upon the ability to rapidly synthesize sugar phosphates. Compared with chemical synthesis, enzymatic (kinase) routes to sugar phosphates would be attractive for this application. This work focuses upon the development of a high-throughput colorimetric galactokinase (GalK) assay and its application toward probing the substrate specificity and kinetic parameters of Escherichia coli GalK. The demonstrated dinitrosalicylic assay should also be generally applicable to a variety of sugar-processing enzymes.

Synthesis of glycosylated-β(1-4)-amino(methoxy) and -oxyamino carbohydrate analogues

The synthesis of new oligosaccharides containing nitrogen or oxygen-nitrogen in interglycosidic linkage is described. Several modified β-N- and β-O-N linked disaccharides with glucose or galactose as reducing unit such as lactose or cellobiose analogues have been prepared stereoselectively using two different methods. All these compounds were fully characterised by one and two dimensional NMR studies, mass spectroscopy and the crystallographic structure of Gal-β-N-(1,4)-Gal derivative 10 was obtained. These type of structural modifications of oligosaccharides could be useful for study of various biochemical processes.

Regioselective benzoylation of sugars mediated by excessive Bu2SnO: Observation of temperature promoted migration

Regioselective benzoylation of carbohydrates using an excess of dibutyltin oxide (Bu2SnO) at increased reaction temperatures has been developed for the synthesis of several glycoside benzoates with one or two free hydroxyl groups, including gal

A mild and efficient approach for the regioselective silyl-mediated protection-deprotection of C-4 hydroxyl group on carbohydrates

A regioselective route is reported, which makes the free 4-OH group of hexopyranoses and derivatives easily and rapidly available. This protocol shows high efficiency on intermediates, such as 1a, which contain a TIPS protective group at C-6 and necessarily a benzoyl group at C-4. Treatment of 1a with TBAF cleaves the TIPS protecting group and gives rise to an intramolecular migration of the benzoyl group at C-4 to the less crowded C-6 position.