22860-23-7

Basic information

• Product Name: (2R,3S)-2-[(acetyloxy)methyl]-6-oxo-3,6-dihydro-2H-pyran-3,5-diyl diacetate
• Synonyms: (2R,3S)-2-[(acetyloxy)methyl]-6-oxo-3,6-dihydro-2H-pyran-3,5-diyl diacetate
• CAS NO: 22860-23-7
• Molecular Weight: 286.238
• Mol File: 22860-23-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S)-2-[(acetyloxy)methyl]-6-oxo-3,6-dihydro-2H-pyran-3,5-diyl diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-2-[(acetyloxy)methyl]-6-oxo-3,6-dihydro-2H-pyran-3,5-diyl diacetate(22860-23-7)
• EPA Substance Registry System: (2R,3S)-2-[(acetyloxy)methyl]-6-oxo-3,6-dihydro-2H-pyran-3,5-diyl diacetate(22860-23-7)

Safety Data

• Hazardous Substances Data: 22860-23-7(Hazardous Substances Data)

Upstream product

• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 3366-47-0 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose 

Downstream Products

• 1190850-84-0 (2R,4S,5R)-5-(azidomethyl)-4-(benzyloxy)tetrahydrofuran-2-carboxylic acid 
• 605669-67-8 2,5-anhydro-6-azido-3-deoxy-d-ribo-hexonic acid 
• 3238-40-2 furan-2,5-dicarboxylic acid 
• 70117-25-8 methyl 5-(bromomethyl)-furan-2-carboxylate 
• 2144-37-8 methyl 5-(chloromethyl)-2-furoate 
• 6338-41-6 5-hydroxymethyl-furan-2-carboxylic acid 
• 76448-73-2 ethyl 5-(hydroxymethyl)furan-2-carboxylate 
• 36802-01-4 Methyl ester of 5-hydroxymethylfuran 2-carboxylic acid 

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.