53942-33-9

Basic information

• Product Name: 5-(benzoyloxy)-6-[(benzoyloxy)methyl]-2-oxo-5,6-dihydro-2H-pyran-3-yl benzoate
• Synonyms: 5-(benzoyloxy)-6-[(benzoyloxy)methyl]-2-oxo-5,6-dihydro-2H-pyran-3-yl benzoate
• CAS NO: 53942-33-9
• Molecular Formula: C₂₇H₂₀O₈
• Molecular Weight: 472.4429
• Mol File: 53942-33-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(benzoyloxy)-6-[(benzoyloxy)methyl]-2-oxo-5,6-dihydro-2H-pyran-3-yl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(benzoyloxy)-6-[(benzoyloxy)methyl]-2-oxo-5,6-dihydro-2H-pyran-3-yl benzoate(53942-33-9)
• EPA Substance Registry System: 5-(benzoyloxy)-6-[(benzoyloxy)methyl]-2-oxo-5,6-dihydro-2H-pyran-3-yl benzoate(53942-33-9)

Safety Data

• Hazardous Substances Data: 53942-33-9(Hazardous Substances Data)

Upstream product

• 6605-40-9 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 14125-75-8 2,3,4,6-tetra-O-benzoyl-D-hydroxyglucal 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 76514-09-5 2,3,4,6-tetra-O-benzoyl-2-bromo-D-glucono-1,5-lactone 

Downstream Products

• 164169-23-7 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone 
• 53942-34-0 2,4,6-tri-O-benzoyl-3-deoxy-D-arabino-hexono-1,5-lactone 
• 133463-62-4 C₂₀H₁₄O₆ 

Relevant articles and documents

Enantiomerically Pure Building Blocks from Sugars, 9. An Expedient Approach to Pyranoid Ene and Enol Lactones by BF3-Catalyzed Peroxidation of Glycal and Hydroxyglycal Esters

An effective and convenient one-pot procedure, simply involving treatment with boron trifluoride/3-chloroperbenzoic acid (MCPBA), is detailed for the high-yield acquisition of enantiomerically pure dihydropyran-2-ones from mono- and disaccharide-derived glycal and hydroxyglycal esters.An assessment of the scope of the method is given, a total of 17 examples being ample evidence for its preparative utility and apparent generality.Substantiation of the mechanism presented - BF3-promoted removal of the allylic acyloxy group, seizure by MCPBA of the allylcarboxonium ion generated, and fragmentation of the resulting hex-2-enopyranose 1-(3-chloro)perbenzoates on quenching - is provided by characterization of the perester intermediates.Conducting the reaction of glycal esters at room temperature a glycol-type C-1-C-2 bond cleavage occurs instead with the generation of acylated 4,5-dihydroxypentenals.

Photobromination of Carbohydrate Derivatives. Part 4. Observations on Some Glucopyranoside Esters; a Simple Route to Aryl α-L-Idopyranosides

Photobromination of methyl tetra-O-benzoyl-β-D-glucopyranoside gives 2,3,4,6-tetra-O-benzoyl-2-bromo-D-glucono-1,5-lactone as the main product following hydrogen abstraction at C-1, but similar treatment of aryl β-D-glucopyranoside esters causes abstracti