294842-99-2

Upstream product

• 294842-91-4 (S)-Methoxy-phenyl-acetic acid (1R,2R)-2-tert-butoxycarbonylamino-1-(dimethoxy-phosphoryl)-2-phenyl-ethyl ester 
• 140196-38-9 1,1-dimethyl (2-oxo-1-phenylethyl)carbamate 
• 98-88-4 benzoyl chloride 
• 294842-97-0 dimethyl (1R,2R)-2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethylphosphonate 

Relevant academic research and scientific papers

Enantiomeric phosphonate analogs of the docetaxel C-13 side chain

Addition of dimethyl phosphite to racemic N-Boc-phenylglycinal led to a 75:25 mixture of syn and anti dimethyl 2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethylphosphonates. The syn-diastereoisomer was obtained in 50% yield after a single crystallization. Resolution of the syn-isomer was achieved via the (S)-O-methylmandelate esters. Racemization-free ammonolysis gave both enantiomers in high enantiomeric excess. Benzoates of both N-Boc syn-enantiomers were transformed into dimethyl (1R,2R)- and (1S,2S)-2-(benzoylamino)-1-hydroxy-2-phenylethylphosphonates in good yields. Copyright (C) 2000 Elsevier Science Ltd.