103150-32-9

Basic information

• Product Name: TAXOL SIDE CHAIN DIOL(SH)
• Synonyms: TAXOL SIDE CHAIN DIOL(SH)
• CAS NO: 103150-32-9
• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.31108
• Mol File: 103150-32-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: TAXOL SIDE CHAIN DIOL(SH)(CAS DataBase Reference)
• NIST Chemistry Reference: TAXOL SIDE CHAIN DIOL(SH)(103150-32-9)
• EPA Substance Registry System: TAXOL SIDE CHAIN DIOL(SH)(103150-32-9)

Safety Data

• Hazardous Substances Data: 103150-32-9(Hazardous Substances Data)

Upstream product

• 5817-02-7 (1S,2S)-2-amino-1-phenyl-1,3-propanediol 
• 98-88-4 benzoyl chloride 
• 33069-62-4 taxol 
• 688362-68-7 (R)-(+)-N-acetyl-1-phenylprop-2-enylamine 
• 325490-29-7 (1R)-1-phenylprop-2-en-1-amine 
• 226699-14-5 (R)-3-amino-3-phenylprop-1-yne 
• 154614-38-7 (+/-)-N-1-acetyl-1-phenyl-2-propenylamine 
• 123772-66-7 N-(α-phenylpropargyl)acetamide 
• 4393-21-9 1-(phenyl)allylamine 
• 688362-39-2 N-[(1R)-1-phenylprop-2-en-1-yl]benzamide 

Downstream Products

• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 

Relevant articles and documents

Concise synthesis of the Taxol side chain and demethoxy-4-epi-cytoxazone via oxazoline formation through intramolecular benzylic substitution of a bis-trichloroacetimidate

A concise and efficient method for synthesizing the Taxol side chain via the corresponding oxazoline intermediate was developed. The oxazoline ring is formed via an SN1 mechanism to ensure that the trans-oxazoline stereochemistry is retained. This process was induced by intramolecular benzylic substitution of a 1,2-bis-trichloroacetimidate, which was obtained from a known, enantiomerically pure diol. Demethoxy-4-epi-cytoxazone was also obtained from the intermediary trans-oxazoline 3b.

Enantioselective synthesis of 1-aryl-2-propenylamines: A new approach to a stereoselective synthesis of the Taxol side chain

A variety of substituted 1-aryl-2-propenylamines of high enantiomeric purity were prepared via lipase-catalysed resolution of the corresponding racemates. (R)-1-Phenyl-2-propenylamine was further synthesised into (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoic acid methyl ester, the side chain of Taxol.