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Phosphonate analogs of N-benzoyl- and N-Boc-3-phenylisoserine, the taxol C-13 side chain

✍ Scribed by Andrzej E. Wróblewski; Dorota G. Piotrowska

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
710 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

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-phenylethylphosphonate (8a) from the anti isomer 8b was best achieved as O-benzoate 10a or O-trimethylsilyl 9a derivatives. Diethyl 2-(benzoylamino)-lhydroxy-2-phenylethylphosphonate (12a) was efficiently prepared (HCI-AcOEt) from 10a in a one-step procedure. The absolute configuration at C-I in 8a and 8b was established from tH and t3C NMR spectral data of their N,O-isopropylidene derivatives. Acyclic phosphonates from the a series (8, 10, 12) adopt antiperiplanar conformations.

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