482647-80-3

Upstream product

• 331767-00-1 (4S,5R)-4-benzyl-5-[(2R)-2-hydroxy-3-phenylpropyl]-1,3-oxazolidin-2-one 
• 331767-02-3 (4S,5R)-4-benzyl-5-[(2S)-2-azido-3-phenylpropyl]-1,3-oxazolidin-2-one 
• 198208-15-0 (2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane 
• 198208-01-4 (S,E)-tert-butyl 3-oxo-1,6-diphenylhex-4-en-2-ylcarbamate 
• 176504-90-8 dimethyl [(3S)-4-phenyl-3-[N-(tert-butyloxycarbonyl)amino]-2-oxobutyl]phosphonate 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 

Downstream Products

• 482648-05-5 tert-butyl (1S,2S,4S)-4-azido-1-benzyl-2-hydroxy-5-phenylpentylcarbamate 
• 144163-88-2 ((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid tert-butyl ester 
• 144239-99-6 (2S,3R,5S)-2,5-Diamino-1,6-diphenyl-hexan-3-ol 
• 331766-99-5 (4S,5S)-4-benzyl-5-[(2S)-2-azido-3-phenylpropyl]-1,3-oxazolidin-2-one 
• 331767-03-4 tert-butyl (1S,2R,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentylcarbamate 

Relevant academic research and scientific papers

Stereoselective hydroazidation of amino enones: Synthesis of the ritonavir/lopinavir core

(Chemical Equation Presented) The base-catalyzed hydroazidation of α′-amino α,β-unsaturated ketones with in situ generated hydrazoic acid was found to proceed with high stereoselectivity in favor of the syn product. The stereoselectivity is controlled by

Small hydroxyethylene-based peptidomimetics inhibiting both HIV-1 and C. albicans aspartic proteases

We have extended a highly flexible method for rapidly assembling aspartic protease inhibitors to produce symmetric and asymmetric monohydroxyethylene peptidomimetics. This method is based on the prior synthesis of the central non-cleavable peptide-bond is

Epoxyalcohol route to hydroxyethylene dipeptide isosteres. Stereodivergent synthesis of the diamino alcohol core of ritonavir and its C-2 epimer

A stereoselective synthesis of hydroxyethylene dipeptide isosteres based on the 1,4-diamino-2-hydroxybutane structure is described. Horner - Emmons olefination of phosphonates derived from α-amino acids, stereoselective reduction of the resulting enones to allylic alcohols, and syn epoxidation of the latter lead to enantiomerically pure 1-amino-2-hydroxy-3,4-epoxybutanes, key intermediates in the synthesis. Reductive cleavage of the epoxy alcohols with Red-Al proceeds in a highly regioselective way, giving 1-amino-2,4-dihydroxybutanes, from which diamino alcohol hydroxyethylene isosteres are obtained by selective protection of the secondary 2-hydroxy group, via cyclization to 1,3-oxazolidinone, and further elaboration of the 4-hydroxy. Both C-2 epimers of 1,4-diamino-2-hydroxybutanes are accessible by appropriate choice of the conditions for cyclization. The approach is demonstrated by the synthesis of a series of six hydroxyethylene dipeptide isosteres, including the diamino alcohol core of potent HIV-protease inhibitor ritonavir 18 and its C-2 epimer 11a.

Epoxyalcohol route to hydroxyethylene dipeptide isosteres: A new synthesis of the diaminoalcohol core of HIV-protease inhibitor ABT-538 (Ritonavir)

A stereoselective synthesis of the diaminoalcohol core of Ritonavir illustrates a novel approach to hydroxyethylene dipeptide isosteres, based on the regioselective reduction of amino acid-derived epoxyalcohols.