157552-43-7

Basic information

• Product Name: (E,E)-N-phenylmethyl-N-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-O-(2-trimethylsilyl)ethyl carbamic acid
• Synonyms: (E,E)-N-phenylmethyl-N-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-O-(2-trimethylsilyl)ethyl carbamic acid
• CAS NO: 157552-43-7
• Molecular Weight: 455.756
• Mol File: 157552-43-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E,E)-N-phenylmethyl-N-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-O-(2-trimethylsilyl)ethyl carbamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (E,E)-N-phenylmethyl-N-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-O-(2-trimethylsilyl)ethyl carbamic acid(157552-43-7)
• EPA Substance Registry System: (E,E)-N-phenylmethyl-N-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-O-(2-trimethylsilyl)ethyl carbamic acid(157552-43-7)

Safety Data

• Hazardous Substances Data: 157552-43-7(Hazardous Substances Data)

Upstream product

• 80149-80-0 2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate 
• 148458-78-0 Benzyl-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl)-amine 

Downstream Products

• 157552-48-2 (E,E)-N-(12,12,12-trifluoro-3,7-dimethyl-11-trifluoromethyl-2,6,10-dodecatrienyl)-N-phenylmethyl-O-(2-trimethylsilyl)ethyl carbamic acid 
• 157552-55-1 Benzyl-((2E,6E)-3,7-dimethyl-10-oxo-deca-2,6-dienyl)-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 157552-45-9 (E,E)-N-(10-hydroxy-3,7-dimethyl-2,6-decadienyl)-N-phenylmethyl-O-(2-trimethylsilyl)ethyl carbamic acid 
• 157552-46-0 (E,E)-N-(10-iodo-3,7-dimethyl-2,6-decadienyl)-N-phenylmethyl-O-(2-trimethylsilyl)ethyl carbamic acid 
• 157552-44-8 (E,E)-N-<9-(3,3-dimethyl-2-oxiranyl)-3,7-dimethyl-2,6-nonadienyl>-N-phenylmethyl-O-(2-trimethylsilyl)ethyl carbamic acid 

Relevant articles and documents

Farnesyl Chain Modification of Squalene Synthase Inhibitor Benzylfarnesylamine: Conversion to the Terminal Bis(trifluoromethyl) Derivative

Potent squalene synthase inhibitor 1 was converted to the bis(trifluoromethyl) analog 14 in 11percent overall yield for 9 steps.The amine nitrogen of 1 was protected with the 2-(trimethylsilyl)ethoxycarbonyl (TEOC) protecting group.The 10,11 olefin was selectively epoxidized, cleaved and converted to the phosphonium salt 6.The ylid from 6 underwent a Wittig condensation with hexafluoroacetone to give the TEOC containing olefin 8.Tetrabutylammonium fluoride or HF could not remove the TEOC group without isomerizing the 10,11 olefin of the farnesyl chain to the E-9,10 olefin.The bis(trifluoromethyl) olefin of 8 is very sensitive to either acidic or basic conditions.However, it was found that BF3*Et2O could remove the TEOC group without the undesired isomerization to give 14.