956345-29-2

Upstream product

• 3674-06-4 Boc-Phe-ONSu 
• 956345-28-1 C₁₈H₂₆N₂O₆ 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 956345-30-5 C₂₀H₂₉N₃O₆ 
• 956345-31-6 C₂₆H₃₃N₃O₇ 
• 956345-33-8 C₃₄H₄₅N₃O₅Si 
• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 956345-41-8 C₂₁H₃₃N₄O₅PCl₂ 
• 956345-42-9 C₂₁H₃₃N₄O₅PCl₂ 
• 956345-39-4 C₁₇H₂₇N₃O₄ 

Relevant academic research and scientific papers

Synthesis and epimerization of phenylalanyl 4-aminocyclophosphamides

Peptide and amino acid conjugates of (4R)- and (4S)-4-aminocyclophosphamides (4-NH2-CPA, 3) were designed as prodrug forms of phosphoramide mustard. Four diastereomers of Boc-Phe-4-NH-CPA (6) were synthesized stereospecifically from homoserine (R or S) and the protection strategy was optimized for the homoserine hydroxyl group during the construction of the 1,3,2-oxazaphosphorinane ring. The Phe-4-NH-CPA isomers of the trans-configuration ((2S,4R)- and (2R,4S)-) were found to be less stable than the corresponding isomers of the cis-configuration ((2R,4R)- and (2S,4S)-) and to undergo epimerization of the C-4 chiral center in the presence of 25% TFA used during Boc deprotection. The synthetic route developed should be applicable to the synthesis of a variety of peptide and amino acid conjugates of 4-aminocyclophosphamide.