392334-82-6

Basic information

• Product Name: 5-(tert-butyl-diphenyl-silanyloxy)-10-isopropenyl-3-oxo-15-oxa-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12-dien-6-yne-13-carboxylic acid tert-butyl ester
• Synonyms: 5-(tert-butyl-diphenyl-silanyloxy)-10-isopropenyl-3-oxo-15-oxa-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12-dien-6-yne-13-carboxylic acid tert-butyl ester
• CAS NO: 392334-82-6
• Molecular Weight: 610.866
• Mol File: 392334-82-6.mol

Chemical Properties

• CAS DataBase Reference: 5-(tert-butyl-diphenyl-silanyloxy)-10-isopropenyl-3-oxo-15-oxa-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12-dien-6-yne-13-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(tert-butyl-diphenyl-silanyloxy)-10-isopropenyl-3-oxo-15-oxa-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12-dien-6-yne-13-carboxylic acid tert-butyl ester(392334-82-6)
• EPA Substance Registry System: 5-(tert-butyl-diphenyl-silanyloxy)-10-isopropenyl-3-oxo-15-oxa-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12-dien-6-yne-13-carboxylic acid tert-butyl ester(392334-82-6)

Safety Data

• Hazardous Substances Data: 392334-82-6(Hazardous Substances Data)

Upstream product

• 392334-78-0 t-butyl (5S)-12-(t-butyldimethylsilyloxy)-10-(t-butyldiphenylsilyloxy)-5-isopropenyl-3-keto-15-(p-methoxybenzyloxy)-8,13-pentadecadiynoate 
• 392334-80-4 t-butyl (5S)-12-(t-butyldimethylsilyloxy)-10-(t-butyldiphenylsilyloxy)-5-isopropenyl-3-keto-15-iodo-8,13-pentadecadiynoate 
• 392334-79-1 t-butyl (5S)-12-(t-butyldimethylsilyloxy)-10-(t-butyldiphenylsilyloxy)-15-hydroxy-5-isopropenyl-3-keto-8,13-pentadecadiynoate 
• 392686-85-0 (13S)-2-t-butoxycarbonyl-6-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone 
• 392334-77-9 (3S)-10-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-3-isopropenyl-13-(p-methoxybenzyloxy)-6,11-tri ecadiynal 
• 392334-75-7 (11S)-6-(t-butyldiphenylsilyloxy)-13,13-dimethoxy-11-isopropenyl-1-(p-methoxybenzyloxy)-2,7-tridecadiyn-4-ol 
• 392334-76-8 (3S)-8-(t-butyldiphenylsilyloxy)-10-hydroxy-3-isopropenyl-13-(p-methoxybenzyloxy)-6,11-tridecadiynal 
• 392686-86-1 (13S)-2-t-butoxycarbonyl-6-hydroxy-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone 
• 392334-72-4 (8S)-1-(t-butyldimethylsilyloxy)-3-(t-butyldiphenylsilyloxy)-10,10-dimethoxy-8-isopropenyl-4-decyne 
• 392334-73-5 (8S)-3-(t-butyldiphenylsilyloxy)-10,10-dimethoxy-8-isopropenyl-4-decynol 
• 392334-74-6 (8S)-3-(t-butyldiphenylsilyloxy)-10,10-dimethoxy-8-isopropenyl-4-decynal 
• 392334-71-3 (8S)-1-(t-butyldimethylsilyloxy)-10,10-dimethoxy-8-isopropenyl-4-decyn-3-ol 
• 190718-41-3 methyl (S)-6,6-dimethoxy-4-isopropenylhexanoate 
• 190718-83-3 (S)-6,6-dimethoxy-4-isopropenylhexanal 

Relevant articles and documents

Synthesis of (-)-deoxypukalide, the enantiomer of a degradation product of the furanocembranolide pukalide

A convergent stereoselective synthesis of (-)-deoxypukalide is described. This substance has not yet been found in Nature but is obtained through deoxygenation of pukalide, the first naturally occurring furanocembrane to be structurally elucidated. The route features a new intraannular furan synthesis that entails treatment of a 4-oxopropargylic β-keto ester with silica gel. The product of this novel reaction, a 3-carboxy 2,5-bridged furan, is formed in 96% yield. The synthetic strategy was strongly directed by molecular mechanics calculations, which provided valuable insight into stereodefining steps including double bond stereochemistry and butenolide configuration.