287478-47-1

Basic information

• Product Name: (1R,4aR,10aS)-7-Formyl-1,4a,7-trimethyl-6-phenylsulfanyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester
• Synonyms: (1R,4aR,10aS)-7-Formyl-1,4a,7-trimethyl-6-phenylsulfanyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester
• CAS NO: 287478-47-1
• Molecular Weight: 426.62
• Mol File: 287478-47-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1R,4aR,10aS)-7-Formyl-1,4a,7-trimethyl-6-phenylsulfanyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4aR,10aS)-7-Formyl-1,4a,7-trimethyl-6-phenylsulfanyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester(287478-47-1)
• EPA Substance Registry System: (1R,4aR,10aS)-7-Formyl-1,4a,7-trimethyl-6-phenylsulfanyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester(287478-47-1)

Safety Data

• Hazardous Substances Data: 287478-47-1(Hazardous Substances Data)

Upstream product

• 78-85-3 2-methylpropenal 
• 287401-06-3 (1R,4aR,8aS)-1,4a-Dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-1,2,3,4,4a,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 391277-80-8 (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 287401-10-9 (1R,4aR,5S,8aS)-5-Ethynyl-5-hydroxy-1,4a-dimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 467222-25-9 (1R,4aR,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 308795-75-7 (1R,4aR,8aS)-5-Ethynyl-5-hydroxy-1,4a-dimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 287401-08-5 CH₂CH₂COCHC₂CH₃CO(CH₂)3CH₂CH₂OCO₂CH₃HCH₂OCH₂ 
• 287401-09-6 CH₂CH₂COCHC₂CH₃CO(CH₂)3CH₂CH₂OCOCH₃HCH₃H 
• 287401-07-4 CH₂CH₂COCHC₂CH₃CO(CH₂)3CH₂CH₂OCO₂CH₃H 
• 117556-90-8 (8aR)-3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione 1-ethylene ketal 
• 100348-93-4 (R)-Wieland-Miescher ketone 

Downstream Products

• 119290-87-8 Acanthoic acid 

Relevant articles and documents

INTERLEUKIN-1 AND TUMOR NECROSIS FACTOR-A MODULATORS; SYNTHESES OF SUCH MODULATORS AND METHODS OF USING SUCH MODULATORS

Compounds are disclosed that have the chemical structure of Formula (II), (IIA) and (IIB) and their prodrug esters and acid-addition salts, and that are useful as Interleukin-1 and Tumor Necrosis Factor-a modulators, and thus are useful in the treatment of various diseases, wherein the R groups are defined in the claims.

Enantioselective synthesis of the antiinflammatory agent (-)-acanthoic acid

An enantioselective synthesis of the potent antiinflammatory agent (-)-acanthoic acid (1) is described. The successful strategy departs from (-)-Wieland-Miescher ketone (10), which is readily available in both enantiomeric forms and constitutes the starting point toward a fully functionalized AB ring system of 1. Conditions were developed for a regioselective double alkylation at the C4 center of the A ring, which produced compound 32 as a single stereoisomer. Construction of the C ring of 1 was accomplished via a Diels-Alder reaction between sulfur-containing diene 43 and methacrolein (36), which after desulfurization and further functionalization yielded synthetic acanthoic acid. The described synthesis confirms the proposed stereochemistry of the natural product and represents a fully stereocontrolled entry into an underexplored class of biologically active diterpenes.