13143-91-4

Basic information

• Product Name: methyl 2,3-di-O-benzoylpentopyranoside
• CAS NO: 13143-91-4
• Molecular Formula: C₂₀H₂₀O₇
• Molecular Weight: 372.3686
• Mol File: 13143-91-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 546.5°C at 760 mmHg
• Flash Point: 193.3°C
• Density: 1.32g/cm³
• Vapor Pressure: 8.9E-13mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: methyl 2,3-di-O-benzoylpentopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-benzoylpentopyranoside(13143-91-4)
• EPA Substance Registry System: methyl 2,3-di-O-benzoylpentopyranoside(13143-91-4)

Safety Data

• Hazardous Substances Data: 13143-91-4(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 91-09-8 methyl β-L-arabinopyranoside 
• 5328-37-0 L-arabinose 

Relevant articles and documents

Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics

Albomycins are peptidyl thionucleoside natural products that display antimicrobial activity against clinically important pathogens. Their structures are characterized by a thioheptose with atypical stereochemistry including a d-xylofuranose ring modified with a d-amino acid moiety. Herein it is demonstrated that AbmH is a pyridoxal 5′-phosphate (PLP)-dependent transaldolase that catalyzes a threo-selective aldol-type reaction to generate the thioheptose core with a d-ribofuranose ring and an l-amino acid moiety. The conversion of l-to d-amino acid configuration is catalyzed by the PLP-dependent epimerase AbmD. The d-ribo to d-xylo conversion of the thiofuranose ring appears according to gene deletion experiments to be mediated by AbmJ, which is annotated as a radical S-adenosyl-l-methionine (SAM) enzyme. These studies establish several key steps in the assembly of the thioheptose core during the biosynthesis of albomycins.

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.