4137-35-3

Basic information

• Product Name: methyl 2,3-bis-O-benzoyl-α-D-galactopyranoside
• Synonyms: methyl 2,3-bis-O-benzoyl-α-D-galactopyranoside
• CAS NO: 4137-35-3
• Molecular Weight: 402.401
• Mol File: 4137-35-3.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: methyl 2,3-bis-O-benzoyl-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-bis-O-benzoyl-α-D-galactopyranoside(4137-35-3)
• EPA Substance Registry System: methyl 2,3-bis-O-benzoyl-α-D-galactopyranoside(4137-35-3)

Safety Data

• Hazardous Substances Data: 4137-35-3(Hazardous Substances Data)

Upstream product

• 7647-01-0 hydrogenchloride 
• 67-64-1 acetone 
• 6748-85-2 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 64-19-7 acetic acid 
• 98-88-4 benzoyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 4056-12-6 methyl 4,6-O-(phenylborylene)-α-D-glucopyranoside 
• 122971-00-0 methyl O²,O³-dibenzoyl-O⁴,O⁶-phenylboranediyl-α-D-glucopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 1112986-37-4 C₂₉H₂₈O₉ 
• 3601-36-3 methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside 
• 31505-55-2 methyl 2,3-di-O-benzoyl-6-O-triphenylmethyl-α-D-galactopyranoside 
• 4288-93-1 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 61553-58-0 methyl 4,6-di-O-acetyl-2,3,-di-O-benzoyl-α-D-glucopyranoside 
• 20231-37-2 methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-6-O-trityl-α-D-glucopyranoside 
• 57784-06-2 methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 
• 23397-70-8 methyl 2,3-di-O-benzoyl-4,6-di-O-tosyl-α-D-glucopyranoside 
• 1232681-97-8 O1-methyl-(O2,O3-dibenzoyl-O6-diphenylphosphoryl-α-D-glucopyranoside) 

Relevant articles and documents

Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides

A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is

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.

Highly Regioselective Monoacylation of Unprotected Glucopyranoside Using Transient Directing-Protecting Groups

The regioselective functionalization of monosaccharides is notoriously achieved using metal catalysis, lengthy synthetic strategies requiring protection/deprotection, various enzymes, or other methods that target cis-diols (and thus cannot be used with glucopyranose derivatives), In this paper, we report a new method using selected boronic acids as temporary protecting groups, and describe its application to the regioselective functionalization of methyl α-d-glucopyranoside, the most difficult monosaccharide to functionalize regioselectively. Generally, reactions of glucopyranosides may lead to a plethora of mono- and polyfunctionalized derivatives, yet our method gave the 3-O-acetylated, 2-O-benzoylated, and 2-O-pivaloylated derivatives of methyl α-d-glucopyranoside as major products. We focused on the use of recyclable and green temporary protecting groups (in a one-pot reaction) and on the modulation of the intramolecular hydrogen-bonding network using selected arylboronic acids. A complete scalable procedure leading to a single regioisomer from unprotected methyl α-d-glucopyranoside is presented.