864251-39-8

Basic information

• Product Name: 1,3-dibenzyloxy-2-propyl acetoacetate
• Synonyms: 1,3-dibenzyloxy-2-propyl acetoacetate
• CAS NO: 864251-39-8
• Molecular Weight: 356.419
• Mol File: 864251-39-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,3-dibenzyloxy-2-propyl acetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dibenzyloxy-2-propyl acetoacetate(864251-39-8)
• EPA Substance Registry System: 1,3-dibenzyloxy-2-propyl acetoacetate(864251-39-8)

Safety Data

• Hazardous Substances Data: 864251-39-8(Hazardous Substances Data)

Upstream product

• 20194-18-7 sodium phenyl-methanolate 
• 6972-79-8 dibenzyl glycerol 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 158976-92-2 1,3-dibenzyloxy-2-propyl-diazoacetate 

Relevant articles and documents

Enantioselective Syntheses of 2-Deoxyxylono-1,4-lactone and 2-Deoxyribono-1,4-lactone from 1,3-Dioxan-5-yl Diazoacetates

1,3-Dioxan-5-yl diazoacetates are valuable substrates for highly diastereoselective and enantio-selective carbon-hydrogen insertion reactions. trans-2-(tert-Butyl)-1,3-dioxan-5-yl diazoacetate is a direct precursor to 2-deoxyribono-1,4-lactone in up to 81% ee, whereas cis-2-(tert-butyl)-1,3-dioxan-5-yl diazoacetate yields only the protected 2-deoxyxylono-1,4-lactone in up to 96% ee. However, trans-2-aryl-1,3-dioxan-5-yl diazoacetate (aryl = phenyl or 2-naphthyl) forms the precursor to 2-deoxyxylono-1,4-lactone in up to 95% ee but with the mirror image configuration of that produced from the trans-2-(tert-butyl) analogue. The catalysts that are most suitable for these carbon-hydrogen insertion reactions are chiral dirhodium(II) carboxamidates. 1,3-Dialkoxy-2-propyl diazoacetates give mainly 2-deoxyxylono-1,4-lactone derivatives (>90:10) with generally high enantiocontrol, but replacement of hydrogen at the 2-position of these 2-propyl diazoacetates led to a mixture of products.

SYNTHESIS OF 2-DEOXYXYLOLACTONE FROM GLYCEROL DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE CARBON-HYDROGEN INSERTION REACTIONS

diazodecomposition of 1,3-dialkoxy-2-propyl diazoacetates catalyzed by chiral dirhodium(II) carboxamides results in highly enantioselective and diastereoseelctive carbon-hydrogen insertion which forms 3,5-dialkyl 2-deoxyxylolactones in up to 98percent enantiomeric excess.