60551-04-4

Basic information

• Product Name: Methyl 2,4-Di-O-benzoyl-β-L-arabinopyranoside
• Synonyms: Methyl 2,4-Di-O-benzoyl-β-L-arabinopyranoside
• CAS NO: 60551-04-4
• Molecular Weight: 372.375
• Mol File: 60551-04-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methyl 2,4-Di-O-benzoyl-β-L-arabinopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,4-Di-O-benzoyl-β-L-arabinopyranoside(60551-04-4)
• EPA Substance Registry System: Methyl 2,4-Di-O-benzoyl-β-L-arabinopyranoside(60551-04-4)

Safety Data

• Hazardous Substances Data: 60551-04-4(Hazardous Substances Data)

Upstream product

• 65914-27-4 Methyl 2-O-benzoyl-3,4-O-(S)-benzylidene-β-L-arabinopyranoside 
• 65914-29-6 endo-methyl 2-O-benzoyl-3,4-O-benzylidene-β-L-arabinopyranoside 
• 98-88-4 benzoyl chloride 
• 91-09-8 methyl β-L-arabinopyranoside 

Relevant articles and documents

Regioselective Ring Opening of Selected Benzylidene Acetals. A Photochemically Initiated Reaction for Partial Deprotection of Carbohydrates

A new method is described for regioselective partial deprotection of carbohydrates protected as benzylidene acetals.This deprotection was accomplished for each of the six methyl pyranosides (4,5, and 18-21) studied by irradiation of the protected sugar and N-bromsuccinimide (NBS) in the presence of water.Under these conditions the benzylidene (1,3-dioxolane) ring in each compound opened to give a methyl pyranoside with an axial benzoyloxy group and an equatorial hydroxy group.For example, irradiation of methyl 3,4-O-benzylidene (R or S)-6-deoxy-2-O-(2,2-dimethylpropanoyl)-α-L-galactopyranoside (18 or 19) with NBS, barium carbonate, and water resulted in the formation of methyl 4-O-benzoyl-6-deoxy-2-O-(2,2-dimethylpropanoyl)-α-L-galactopyranoside (22) in 72percent yield.In a similar manner compounds 4 and 5 gave 10 and compounds 20 and 21 produced 23.The advantages of the deprotection process are described.

Regioselective Monoacylation of Some Glycopyranosides via Cyclic Tin Intermediates

Selective mono-benzoylation of some pento- and hexo-pyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me-β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) by using Bu2SnO was examined in comparaison with the results of the (Bu3Sn)2O method and direct benzoylation.The Bu2SnO method is particularly useful in that it selectively activates an equatorial hydroxyl group wich bears an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary OH group.The various mono- and di-O-benzoyl derivatives prepared in this work were unambiguously identified by analysis of their 13C-nuclear magnetic resonance spectra.