20126-72-1

Basic information

• Product Name: 6-[(S)-2,3-Dihydroxy-3-methylbutyl]-7-hydroxycoumarin
• Synonyms: (-)-6-[(S)-2,3-Dihydroxy-3-methylbutyl]-7-hydroxy-2H-1-benzopyran-2-one;6-[(S)-2,3-Dihydroxy-3-methylbutyl]-7-hydroxy-2H-1-benzopyran-2-one;6-[(S)-2,3-Dihydroxy-3-methylbutyl]-7-hydroxycoumarin;7-Demethyl-2',3'-dihydroxydihydrosuberosine;Peucedanol
• CAS NO: 20126-72-1
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.27
• Mol File: 20126-72-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-[(S)-2,3-Dihydroxy-3-methylbutyl]-7-hydroxycoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[(S)-2,3-Dihydroxy-3-methylbutyl]-7-hydroxycoumarin(20126-72-1)
• EPA Substance Registry System: 6-[(S)-2,3-Dihydroxy-3-methylbutyl]-7-hydroxycoumarin(20126-72-1)

Safety Data

• Hazardous Substances Data: 20126-72-1(Hazardous Substances Data)

Upstream product

• 325137-96-0 6-[(1R,2S)-1,2-epoxy-3-hydroxy-3-methylbutyl]-7-(methoxymethoxy)chromen-2-one 
• 325137-94-8 7-(methoxymethoxy)-6-(trifluoromethanesulfonyl)chromen-2-one 
• 325137-90-4 6-[(1R,2S)-1,2-epoxy-3-oxobutyl]-7-(methoxymethoxy)chromen-2-one 
• 325137-92-6 7-(methoxymethoxy)-6-[(E)-3-oxo-1-butenyl]chromen-2-one 
• 325138-04-3 7-(methoxymethoxy)-6-[(Z)-3-oxo-1-butenyl]chromen-2-one 
• 202350-87-6 6-hydroxy-7-(methoxymethoxy)-2H-chromen-2-one 
• 325138-02-1 6-formyl-7-(methoxymethoxy)chromen-2-one 
• 305-01-1 aesculetin 
• 616241-73-7 6-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-(methoxymethoxy)chromen-2-one 

Downstream Products

• 495-32-9 marmesin 
• 25245-91-4 decursin 
• 5993-18-0 decursinol 

Relevant articles and documents

Enantioselective total syntheses of (+)-decursin and related natural compounds using catalytic asymmetric epoxidation of an enone

The enantioselective total syntheses of (+)-decursin (1) and related natural dihydropyranocoumarins (-)-prantschimgin (3), (+)-decursinol (4), and (+)-marmesin (5) were achieved for the first time using catalytic asymmetric epoxidation of an enone as the key step. Catalytic asymmetric epoxidation of the enone was effectively promoted by the novel multifunctional asymmetric catalyst generated from La(O-i-Pr)3, BINOL, and Ph3As=O in a 1:1:1 ratio to afford epoxide in 94% yield and 96% ee, which was recrystallized to give optically pure epoxide. After conversion to the common key intermediate (-)-peucedanol (7), all natural dihydropyranocoumarins were synthesized through palladium-catalyzed intramolecular C-O coupling reactions. A possible reaction mechanism of the catalytic asymmetric epoxidation of enones is also described based on X-ray analysis, laser desorption/ionization time-of-flight mass spectrometry, kinetic studies, and asymmetric amplification studies.

Enantioselective total syntheses of novel PKC activator (+)-decursin and its derivatives using catalytic asymmetric epoxidation of an enone

The catalytic asymmetric total syntheses of (+)-decursin and three related natural products, (+)-decursinol, (-)-prantschimgin and (+)-marmesin, were achieved for the first time using catalytic asymmetric epoxidation of an enone as the key step. The catalytic asymmetric epoxidation of enone was found to be promoted effectively by novel multifunctional asymmetric catalyst generated from La(O-i-Pr)3, BINOL and O=AsPh3 in a 1:1:1 ratio to afford epoxide in 94% yield and 96% ee, which was recrystallized to give the optically pure epoxide. (C) 2000 Elsevier Science Ltd.