Improved large-scale synthesis of phenylisoserine and the taxol C-13 side chain

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 407-409

  Voronkov, Michael V ^a   Gontcharov, Alexander V ^a   Wang, Zhi Min ^a  

^a LEXICON PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; BENZONITRILE; CINNAMIC ACID DERIVATIVE; ESTER DERIVATIVE; PACLITAXEL; PHENYLISOSERINE; PROPIONIC ACID DERIVATIVE; SERINE DERIVATIVE; SULFURIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 0037421084     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02434-6     Document Type: Article

References (14)

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12. 8 mp 222-224°C). Hydroxyaminoacids 3b and 3c were prepared according to the similar procedure.
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14. Literature suggests that acidic hydrolysis of the oxazoline leads to the equilibrium mixture of N- and O-benzoyl derivatives. In our case, only the former derivative had crystallized out of the acidic aqueous solution, while the latter remained dissolved. See: Bunnage M.E., Davies S.G., Goodwin C.J. J. Chem. Soc., Perkin Trans. 1. 1993;1375. and references cited therein.