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

✍ Scribed by Michael V Voronkov; Alexander V Gontcharov; Zhi-Min Wang

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
68 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Dihydrodihydroxycinnamic acids and their esters react with acetonitrile or benzonitrile in the presence of sulfuric acid to afford the corresponding syn-b-amino-a-hydroxypropionic acid derivatives. High yields and diastereoselectivity of this transformation allows preparation of various phenylisoserine derivatives on a practical scale.

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Phosphonate analogs of N-benzoyl- and N-
Phosphonate analogs of N-benzoyl- and N-Boc-3-phenylisoserine, the taxol C-13 side chain
✍ Andrzej E. WrΓ³blewski; Dorota G. Piotrowska πŸ“‚ Article πŸ“… 1998 πŸ› Elsevier Science 🌐 French βš– 710 KB

Diastereoselectivity of the addition of diethyl phosphite to N-Boc-phenylglycinal reached 50% when NEh or KF were used as catalysts but employing lithium diethyl phosphonate lower de. was obtained. Separation of the required syn diethyl 2-[(tert.butoxycarbonyl)amino]-I-hydroxy-2-phenylethylphosphona