247575-97-9

Upstream product

• 247575-76-4 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (1S,2S,3S)-3-dibenzylamino-1-((S)-1-dibenzylamino-2-phenyl-ethyl)-2-hydroxy-4-phenyl-butyl ester 
• 247575-73-1 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-2-dibenzylamino-3-phenyl-propyl ester 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 

Downstream Products

• 129491-64-1 (2S,3S,4S,5S)-2,5-bis<<(tert-butyloxy)carbonyl>amino>-3,4-dihydroxy-1,6-diphenylhexane 
• 134878-06-1 (2S,3S,4S,5S)-2,5-diamino-1,6-diphenyl-3,4-hexanediol 

Relevant academic research and scientific papers

Design, synthesis, evaluation, and crystallographic-based structural studies of HIV-1 protease inhibitors with reduced response to the V82A mutation

In our quest for HIV-1 protease inhibitors that are not affected by the V82A resistance mutation, we have synthesized and tested a second generation set of C2-symmetric HIV-1 protease inhibitors that contain a cyclohexane group at P1 and/or P1′

Facile and highly stereoselective synthesis of the C2-symmetrical diamino diol core-unit of HIV-1 protease inhibitors and of their symmetrical and unsymmetrical analogs from lithiated 2-(dibenzylamino)alkyl carbamates: Oxidative dimerization

The lithio derivatives of (S)-and (R)-2-(N,N-dibenzylamino)alkyl carbamates 3 and ent-3, generated by substrate-directed deprotonation from the precursors 2 and ent-2, add with high diastereoselectivity to (S)-2-(N,N- dibenzylamino)alkanals. The (S)-aminoaldehyde 5a, derived from (S)- phenylalanine, is produced in situ from the lithium compound 3a by the controlled addition of dioxygen to the reaction mixture affording the protected anti,syn,anti-α,δ-diamino-β,γ-diol 6aa which is the core unit of anti-HIV 1 protease agents. Several symmetric and unsymmetric structure analogs, differing in the substitution pattern and the configurations, have been synthesized. A further approach to the title compound is given by the acylation of lithium derivatives 3/4, followed by a hydride reduction. The reaction of the lithium derivatives 3a/4a with CuCl leads to an eliminative oxidative coupling with formation of (3 E/Z, 2S,5S)-2,5-dibenzylamino-1,6- diphenylhex-3-enes (E)- and (Z)-26.