425681-12-5

Basic information

• Product Name: (E)-3-homogeranyl-4-(tert-butyldiphenylsilyloxy)benzene
• Synonyms: (E)-3-homogeranyl-4-(tert-butyldiphenylsilyloxy)benzene
• CAS NO: 425681-12-5
• Molecular Weight: 482.781
• Mol File: 425681-12-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (E)-3-homogeranyl-4-(tert-butyldiphenylsilyloxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-homogeranyl-4-(tert-butyldiphenylsilyloxy)benzene(425681-12-5)
• EPA Substance Registry System: (E)-3-homogeranyl-4-(tert-butyldiphenylsilyloxy)benzene(425681-12-5)

Safety Data

• Hazardous Substances Data: 425681-12-5(Hazardous Substances Data)

Upstream product

• 331233-75-1 (E)-4-(4,8-dimethylnona-3,7-dien-1-yl)phenol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 425681-14-7 diethyl ((E)-4,8-dimethyl-3,7-nonadienyl)phosphonate 
• 623-12-1 4-chloromethoxybenzene 
• 824-94-2 p-methoxybenzyl chloride 
• 38011-83-5 trans-1-(4,8-dimethylnona-3,7-dien-1-yl)-4-methoxybenzene 
• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 

Downstream Products

• 15340-76-8 1,1,4aβ-trimethyl-1,2,3,4,4a,9,10,10a-octahydro-10aα-phenanthren-6-ol 

Relevant articles and documents

Enantio- and diastereoselective stepwise cyclization of polyprenoids induced by chiral and achiral LBAs. A new entry to (-)-ambrox, (+)-podocarpa-8,11,13-triene diterpenoids, and (-)-tetracyclic polyprenoid of sedimentary origin

An enantio- and diastereoselective stepwise cyclization of polyprenoids induced by Lewis acid-assisted chiral Bronsted acids (chiral LBAs) and achiral LBAs is described. In particular, the absolute stereocontrol in the initial cyclization of polyprenoids to form an A-ring induced by chiral LBAs and the importance of the nucleophilicity of the internal terminator in polyprenoids for the relative stereocontrol in subsequent cyclization are demonstrated. (-)-Ambrox was synthesized via the enantioselective cyclization of (E,E)-homofarnesyl triethyrsily ether with triethylsilyl ether with tin(IV) chloride-coordinated (R)-2-(o-fluorobenzyloxy)-2′-hydroxy-1,1′-binaphthyl ((R)-BINOL-o-FBn) and subsequent diastereoselective cyclization with CF3CO2H·SnCl4 as key steps. Protection of (E,E)-homofarnesol by a triethylsilyl group increased the enantioselectivity of chiral LBA-induced cyclization and both the chemical yield and diastereoselectivity in the subsequent cyclization. The enantioselective cyclization of homo(polyprenyl)arenes possessing an aryl group was also induced by (R)-BINOL-o-FBn·SnCl4. Several optically active podocarpa-8,11,13-triene diterpenoids and (-)-tetracyclic polyprenoid of sedimentary origin were synthesized (75-80% ee) by the enantioselective cyclization of homo(polyprenyl)benzene derivatives induced by (R)-BINOL-o-FBn·SnCl4 and subsequent diastereoselective cyclization induced by BF3-Et2O/EtNO2 or CF3CO2H·SnCl4.