21056-53-1

Upstream product

• 98-88-4 benzoyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 4056-12-6 methyl 4,6-O-(phenylborylene)-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 
• 709-50-2 methyl beta-D-glucopyranoside 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 50-69-1 D-ribose 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 66464-15-1 methyl 2-O-benzoyl-6-O-trityl-α-D-glucopyranoside 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-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 

Downstream Products

• 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 
• 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 
• 26927-44-6 methyl 2,6-di-O-benzoyl-α-D-glycopyranoside 
• 1073186-56-7 methyl O²-benzoyl-O⁶-p-toluenesulfonyl-α-D-glucoside 
• 127446-61-1 methyl 2-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-methylsulfonyl-α-D-glucopyranoside 
• 127446-60-0 methyl 2-O-benzoyl-6-O-(tert-butyldimethylsilyl)-3,4-di-O-methylsulfonyl-α-D-glucopyranoside 
• 148657-22-1 methyl 2-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-3,4-dideoxy-α-D-hex-3-enopyranoside 
• 127446-62-2 methyl 6-O-(tert-butyldiphenylsilyl)-3,4-dideoxy-α-D-erythro-hex-3-enopyranoside 
• 66464-15-1 methyl 2-O-benzoyl-6-O-trityl-α-D-glucopyranoside 
• 51385-37-6 methyl 2-O-benzoyl-3,4-di-O-methanesulfonyl-6-O-trityl-α-D-glucopyranoside 
• 148657-21-0 methyl 2-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-glucopyranoside 

Relevant academic research and scientific papers

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

Lanthanum-catalyzed aqueous acylation of monosaccharides by benzoyl methyl phosphate

It was previously reported that diols dissolved in water (pH 8, EPPS buffer) react with benzoyl methyl phosphate (BMP) in the presence of lanthanide ions to form monobenzoyl esters. We have investigated the possibility of extending this process to include

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

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.

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.

Selectivity switch in the catalytic functionalization of nonprotected carbohydrates: Selective synthesis in the presence of anomeric and structurally similar carbohydrates under mild conditions

A catalytic process for the chemo- and regioselective functionalization of nonprotected carbohydrates has been developed. This novel process allows selective thiocarbonylation, acylation, and sulfonylation of a particular hydroxy group in a particular carbohydrate in the simultaneous presence of structurally similar carbohydrates such as anomers. In addition, the chemoselectivity can be switched by regulating only the length of the alkyl chain in the organotin catalyst.

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.

Regioselective protection of sugars catalyzed by dimethyltin dichloride

(Chemical Equation Presented) The first catalytic process for protection of hydroxyl groups in sugars has been developed. Highly regioselective protection was accomplished along with high chemical yield. The regioselectivity of the benzoylation was realiz

Chelation-controlled regioselectivity in the lanthanum-promoted monobenzoylation of monosaccharides in water

Monosaccharides are selectively converted to monobenzoates in a base-catalyzed reaction with benzoyl methyl phosphate (BzMP) and a lanthanum salt in water. Yields are reported in terms of formation of the ester, which competes with hydrolysis of BzMP, to

Regioselective acylation of secondary hydroxyl groups by means BOP-Cl

Methyl 2-O-acyl α-D-glucopyranosides are regioselectively formed with good yields by acylation of the correspondent 6-O-trityl pyranosides with carboxylic acids and (BOP-Cl). No acyl migration was observed in the deblocking of the primary hydroxyl group w