142759-87-3

Basic information

• Product Name: (1R,4aR,4bS,7S,10aR)-1,4a,7-Trimethyl-1-phenylsulfanylmethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthrene
• CAS NO: 142759-87-3
• Molecular Weight: 380.638
• Mol File: 142759-87-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,4aR,4bS,7S,10aR)-1,4a,7-Trimethyl-1-phenylsulfanylmethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4aR,4bS,7S,10aR)-1,4a,7-Trimethyl-1-phenylsulfanylmethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthrene(142759-87-3)
• EPA Substance Registry System: (1R,4aR,4bS,7S,10aR)-1,4a,7-Trimethyl-1-phenylsulfanylmethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthrene(142759-87-3)

Safety Data

• Hazardous Substances Data: 142759-87-3(Hazardous Substances Data)

Upstream product

• 3730-56-1 pimara-8⁽¹⁴⁾,15-dien-18-oic acid methyl ester 
• 127-27-5 pimaric acid 
• 1686-59-5 8⁽¹⁴⁾,15-pimaradien-18-ol 
• 108-98-5 thiophenol 

Relevant articles and documents

Partial Synthesis of 9,10-Syn Diterpenes via Tosylhydrazone Reduction: (-)-(9β)-Pimara-7,15-diene and (-)-(9β)-Isopimaradiene

(9β)-Pimara-7,15-diene (3), a proposed intermediate in the biosynthesis of the momilactone phytoalexins (1 and 2) from rice, and its C-13 epimer, (9β)-isopimara-7,15-diene (4), were synthesized from methyl pimara- and isopimara-8,15-dien-18-oates (8b and 8a, respectively).Allylic oxidation of 8a and 8b as well as the derived diterpene hydrocarbons 15a and 15b with chromium trioxide-dipyridine complex afforded 8,15-dien-7-ones 9a, 9b, 16a, and 16b (35-54percent).Lithium-ammonia reduction of 9a, 16a, and 16b gave predominantly trans,anti,trans-isopimara- and -pimara-15-en-7-ones 10, 17a, and 17b.In contrast, catecholborane reduction of the tosylhydrazones of 9a and 9b provided methyl (9β)-isopimara- and (9β)-pimara-7,15-dien-20-oates (23a and 23b) having the 9,10-syn stereochemistry.The parent diterpenes, 3 and 4, were obtained by carboxyl-to-methyl conversions.In a collaborative investigation 3 was tentatively identified as one of five diterpene hydrocarbons produced upon incubation of (E,E,E)-geranylgeranyl pyrophosphate with a crude enzyme extract from UV-treated rice plants.