442913-26-0

Basic information

• Product Name: (1S,4S)-2-{(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enoyl}-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one
• Synonyms: (1S,4S)-2-{(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enoyl}-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one
• CAS NO: 442913-26-0
• Molecular Weight: 513.793
• Mol File: 442913-26-0.mol

Chemical Properties

• CAS DataBase Reference: (1S,4S)-2-{(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enoyl}-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4S)-2-{(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enoyl}-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one(442913-26-0)
• EPA Substance Registry System: (1S,4S)-2-{(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enoyl}-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one(442913-26-0)

Safety Data

• Hazardous Substances Data: 442913-26-0(Hazardous Substances Data)

Upstream product

• 19810-31-2 Benzyloxyacetyl chloride 
• 442913-23-7 (1R,4S)-2-aza-4,5,5-trimethylbicyclo[2.2.1]heptan-3-one 
• 442913-24-8 (1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one 
• 24502-08-7 (E)-4-methylpent-2-enal 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 442913-25-9 (1S,4S)-2-{(2S,3R,4E)-3-hydroxy-6-methyl-2-[(phenyl)methoxy]hept-4-enoyl}-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one 

Downstream Products

• 442913-34-0 (3S,6S)-6-[((2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-(phenylmethoxy)non-6-enoyl)amino]-2,3,4,5,6,7-hexahydro-1-methyl-7-oxoazepin-3-yl acetate 
• 442913-29-3 (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide 
• 442913-22-6 S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate 
• 442913-27-1 (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enal 
• 442913-41-9 S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate 

Relevant articles and documents

The development of a convergent and efficient enantioselective synthesis of the bengamides via a common polyol intermediate

An efficient, general synthetic route to the bengamide family of antitumor agents from a common polyol thioester is described. Consecutive aldol condensations afford the protected polyol thioester side chain suitable for coupling to the bengamides. A novel chiral-phase-transfer-catalyzed enantioselective alkylation affords the properly functionalized caprolactams required for the synthesis of more-complex members of the bengamide family. Use of the methyl 2-naphthyl ether protecting group, compatible with the boron Lewis acids required for enantioselective aldol condensation, allows direct access to all the bengamides.

A Practical Enantioselective Total Synthesis of the Bengamides B, E, and Z

(equation presented) A practical total synthesis of Bengamides B, E, and Z from a common polyol intermediate is described. Consecutive aldol condensations afford a protected polyol thioester side chain suitable for coupling to the Bengamides. A novel chiral phase transfer catalyzed enantioselective alkylation affords the more highly functionalized amino caprolactams required for Bengamides B and Z. Use of the 2-naphthylmethyl ether protecting group, compatible with the boron Lewis acids required for enantioselective aldol condensation, allows direct access to Bengamide B.