137490-44-9

Basic information

• Product Name: ovalicin
• CAS NO: 137490-44-9
• Molecular Weight: 296.364
• Mol File: 137490-44-9.mol

Chemical Properties

• CAS DataBase Reference: ovalicin(CAS DataBase Reference)
• NIST Chemistry Reference: ovalicin(137490-44-9)
• EPA Substance Registry System: ovalicin(137490-44-9)

Safety Data

• Hazardous Substances Data: 137490-44-9(Hazardous Substances Data)

Upstream product

• 157727-76-9 C₈H₁₃Li 
• 215370-56-2 (1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol 
• 166374-52-3 (3S,4S,5S,6R)-5-Methoxy-6-triethylsilanyloxy-1-oxa-spiro[2.5]octan-4-ol 
• 166184-48-1 (3R,4R,5R,6R)-4-(1',5'-dimethylhexa-1',4'-dienyl)-5-methoxy-6-triethylsiloxy-1-oxaspiro<2.5>octan-4-ol 
• 166184-47-0 (3R,5R,6R)-5-methoxy-6-triethylsiloxy-1-oxaspiro<2.5>octan-4-one 
• 91738-34-0 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 870862-60-5 (1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol 
• 870862-57-0 (1R,2R,3S,4S)-1-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexane 
• 870862-47-8 (2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose 
• 870862-49-0 (2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-3-methoxy-6-heptene 
• 870862-48-9 (2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol 
• 870862-50-3 (2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol 
• 870862-52-5 (3S,4R,5S,6S)-6-(tert-butyldiphenylsilanyloxymethyl)-5,6-O-isopropylidenedioxy-4-methoxy-1,7-octadien-3-ol 
• 870862-53-6 (3R,4R,5S,6S)-6-(tert-butyldiphenylsilanyloxymethyl)-5,6-O-isopropylidenedioxy-4-methoxy-1,7-octadien-3-ol 

Relevant articles and documents

Concise enantio- and diastereoselective total syntheses of fumagillol, RK-805, FR65814, ovalicin, and 5-demethylovalicin

(Chemical Equation Presented) L-Proline-mediated α-aminoxylation is a key step in the enantio- and diastereoselective total syntheses of fumagillin, ovalicin, and related compounds (see scheme). These compounds contain a cyclohexane ring, two epoxides, an

Stereoselective total synthesis of (-)-Ovalicin

A new synthetic route for epoxyketone 3 is described, which is a key intermediate in Bartons synthesis of ovalicin (1), a powerful anti-angiogenetic inhibitor, from commercially available d-ribose. The key reactions involved in this synthesis are ring-closing metathesis, Rubottom oxidation and Corey-Chaykovsky epoxidation. The subsequent transformations are carried out according to Bartons strategy to complete the total synthesis of (-)-ovalicin. Georg Thieme Verlag Stuttgart New York.

A diels-alder approach to (-)-ovalicin

A round at the Oval: The antiangiogenic activity of the natural product ovalicin has sparked significant interest. A highly efficient enantio- and diastereoselective total synthesis of ovalicin proved successful in which the key step involved an endo sele

Synthesis of ovalicin starting from D-mannose

A new synthesis of epoxyketone 22 is described that is a key intermediate in Barton's synthesis of ovalicin (2), a powerful anti-angiogenetic inhibitor. The key process for the construction of 22 was ring-closing metathesis of olefins 11 and 12 obtained f

Total synthesis of (-)-ovalicin and analogues from L-quebrachitol

We describe here the first chiral total synthesis of (-)-ovalicin and the synthesis of several related analogues, from the naturally occuring cyclitol L-quebrachitol.

Total synthesis of (-)-Ovalicine from L-Quebrachitol

The first chiral synthesis of (-)-Ovalicine from commercially available L-Quebrachitol in 16 steps and an overall yield of 3.5% is reported.