21056-53-1

Basic information

• Product Name: methyl O²-benzoyl-α-D-glucoside
• Synonyms: methyl O²-benzoyl-α-D-glucoside
• CAS NO: 21056-53-1
• Molecular Weight: 298.293
• Mol File: 21056-53-1.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: methyl O²-benzoyl-α-D-glucoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl O²-benzoyl-α-D-glucoside(21056-53-1)
• EPA Substance Registry System: methyl O²-benzoyl-α-D-glucoside(21056-53-1)

Safety Data

• Hazardous Substances Data: 21056-53-1(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 164398-17-8 <2'S,2''S,4'S,4''S> methyl 2-benzoyl-6-O-(tert-butyldiphenylsilyl)-3-O,4-O-(4',4''-dimethyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 66464-15-1 methyl 2-O-benzoyl-6-O-trityl-α-D-glucopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 50-69-1 D-ribose 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 4056-12-6 methyl 4,6-O-(phenylborylene)-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 

Downstream Products

• 26927-44-6 methyl 2,6-di-O-benzoyl-α-D-glycopyranoside 
• 51385-37-6 methyl 2-O-benzoyl-3,4-di-O-methanesulfonyl-6-O-trityl-α-D-glucopyranoside 
• 66464-15-1 methyl 2-O-benzoyl-6-O-trityl-α-D-glucopyranoside 
• 127446-62-2 methyl 6-O-(tert-butyldiphenylsilyl)-3,4-dideoxy-α-D-erythro-hex-3-enopyranoside 
• 148657-22-1 methyl 2-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-3,4-dideoxy-α-D-hex-3-enopyranoside 
• 127446-60-0 methyl 2-O-benzoyl-6-O-(tert-butyldimethylsilyl)-3,4-di-O-methylsulfonyl-α-D-glucopyranoside 
• 127446-61-1 methyl 2-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-methylsulfonyl-α-D-glucopyranoside 
• 57784-06-2 methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 
• 118918-78-8 methyl 2,4,6-tri-O-benzoyl-α-D-glucopyranoside 
• 1073186-56-7 methyl O²-benzoyl-O⁶-p-toluenesulfonyl-α-D-glucoside 
• 148657-21-0 methyl 2-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-glucopyranoside 
• 261967-65-1 Isophthalic acid 1-((2R,3S,4S,5R,6S)-5-benzoyloxy-3,4-dihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester 3-((2R,3S,4S,5R,6S)-3,4,5-trimethoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester 

Relevant articles and documents

Tin-mediated regioselective acylation of unprotected sugars on solid phase

Methyl α-D-glucopyranoside, methyl α-D-mannopyranoside and methyl β-D-galactopyranoside bound on O-6 to a copolystyrene-DVB resin through a trityl ether linker, have been regioselectively acylated with benzoyl chloride after treatment with Bu2S

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

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.

Magnesium ion enhances lanthanum-promoted monobenzoylation of a monosaccharide in water

Magnesium ion combines selectively with the methyl phosphate by-product in the lanthanum-promoted biomimetic reaction of benzoyl methyl phosphate with monosaccharides.