130273-48-2

Basic information

• Product Name: (3R,4S,5S)-clausenamidone
• Synonyms: (3R,4S,5S)-clausenamidone
• CAS NO: 130273-48-2
• Molecular Weight: 295.338
• Mol File: 130273-48-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3R,4S,5S)-clausenamidone(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5S)-clausenamidone(130273-48-2)
• EPA Substance Registry System: (3R,4S,5S)-clausenamidone(130273-48-2)

Safety Data

• Hazardous Substances Data: 130273-48-2(Hazardous Substances Data)

Upstream product

• 19190-80-8 cis-methyl 2,3-epoxy-3-phenylpropanoate 
• 554420-03-0 (+)-clausenamidonyl (-)-menthoxyacetate 
• 130273-47-1 (3R,4S,5R)-neoclausenamidone 
• 79898-19-4 (2R,3S)-3-phenyloxiranecarboxylic acid 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 115794-67-7 methyl (2R,3S)-3-phenylglycidate 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 173691-07-1 (2R,3S)-2,3-Dihydroxy-N-methyl-N-(2'-phenyl-1',3'-dithiolan-2'-ylmethyl)-3-phenylpropionamide 
• 173691-08-2 (2R,3S)-2,3-Epoxy-N-methyl-N-(2'-phenyl-1',3'-dithiolan-2'-ylmethyl)-3-phenylpropionamide 
• 190771-98-3 (2R,3S)-2,3-Dihydroxy-N-<(2'RS)-2'-hydroxy-2'-phenylethyl>-N-methylpropanamide 
• 173691-06-0 (4R,5S)--2,2-dimethyl-5-phenyl-1,3-dioxolane 
• 122743-18-4 methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate 
• 68579-60-2 2-(methylamino)-1-phenylethanol 
• 132490-26-7 (2R,3S)-phenyl 3-phenyloxirane-2-carboxylate 

Downstream Products

• 1579151-60-2 (+)-(3R,4S,5S)-3-O-acetylclausenamidone 
• 595582-28-8 (±)-(3R,4R,5R,6R)-5-hydroxyclausenamide 
• 722526-35-4 (+)-(3R,4R,5R,6R)-3-O-acetyl-5-hydroxyclausenamide 
• 722526-30-9 (+)-(3R,4R,5R)-3-O-acetyl-5-hydroxyclausenamidone 
• 722526-17-2 (+)-(3R,4R,5R,6S)-3-O-acetyl-5-hydroxyclausenamide 
• 1579151-64-6 (+)-(3R,4R,5S,6R)-3-O-acetyl-5-hydroxyclausenamide 
• 722526-12-7 (±)-(3R,4R,5S,6R)-5-hydroxyclausenamide 
• 722526-06-9 (-)-(3R,4R,5R,6S)-5-hydroxyclausenamide 
• 722526-00-3 (-)-(3R,4S)-Δ^5,6clausenamide 
• 722525-94-2 (-)-(3R,4S)-3-O-acetyl-Δ^5,6clausenamide 
• 595582-27-7 (+)-(3R,4S,5S,6R)-3-O-acetylclausenamide 
• 608128-73-0 (3R,4S,5S,6S)-epi-cis-clausenamide 
• 109905-95-5 (±)-(3R,4S,5S,6R)-clausenamide 

Relevant articles and documents

Enantiomeric resolution, thermodynamic parameters, and modeling of clausenamidone and neoclausenamidone on polysaccharide-based chiral stationary phases

The aim of the paper is to describe a new synthesis route to obtain synthetic optically active clausenamidone and neoclausenamidone and then use high-performance liquid chromatography (HPLC) to determine the optical purities of these isomers. In the process, we investigated the different chromatographic conditions so as to provide the best separation method. At the same time, a thermodynamic study and molecular simulations were also carried out to validate the experimental results; a brief probe into the separation mechanism was also performed. Two chiral stationary phases (CSPs) were compared with separate the enantiomers. Elution was conducted in the organic mode with n-hexane and iso-propanol (IPA) (80/20?v/v) as the mobile phases; the enantiomeric excess (ee) values of the synthetic R-clausenamidone and S-clausenamidone and R-neoclausenamidone and S- neoclausenamidone were higher than 99.9%, and the enantiomeric ratio (er) values of these isomers were 100:0. Enantioselectivity and resolution (α and Rs, respectively) levels with values ranging from 1.03 to 1.99 and from 1.54 to 17.51, respectively, were achieved. The limits of detection and quantitation were 3.6 to 12.0 and 12.0 to 40.0 ug/mL, respectively. In addition, the thermodynamics study showed that the result of the mechanism of chiral separation was enthalpically controlled at a temperature ranging from 288.15 to 308.15?K. Furthermore, docking modeling showed that the hydrogen bonds and π-π interactions were the major forces for chiral separation. The present chiral HPLC method will be used for the enantiomeric resolution of the clausenamidone derivatives.

Preparation of optically active clausenamide derivatives and their therapeutic use.

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An asymmetric total synthesis of (+)-(3R,4S,5R,7S)-neoclausenamide

A new hepatoprotective lactam (+)-(3R,4S,5R,7S)-neoclausenamide 1 isolated from the leaves of Chinese folk medicine Clausena lansium (Lour.) Skeel, has been readily synthesized from methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate in 22.0% overall yield.