482648-05-5

Basic information

• Product Name: Carbamic acid, [(1S,2S,4S)-4-azido-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-, 1,1-dimethylethyl ester
• CAS NO: 482648-05-5
• Molecular Formula: C23H30N4O3
• Molecular Weight: 410.516
• Mol File: 482648-05-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1S,2S,4S)-4-azido-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S,2S,4S)-4-azido-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-, 1,1-dimethylethyl ester(482648-05-5)
• EPA Substance Registry System: Carbamic acid, [(1S,2S,4S)-4-azido-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-, 1,1-dimethylethyl ester(482648-05-5)

Safety Data

• Hazardous Substances Data: 482648-05-5(Hazardous Substances Data)

Upstream product

• 482647-80-3 tert-butyl (1S,2R,4S)-4-azido-1-benzyl-2-hydroxy-5-phenylpentylcarbamate 
• 331767-01-2 Methanesulfonic acid (R)-1-benzyl-2-((4S,5R)-4-benzyl-2-oxo-oxazolidin-5-yl)-ethyl ester 
• 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 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 331766-97-3 tert-butyl (1S,2R,4R)-1-benzyl-2,4-dihydroxy-5-phenylpentylcarbamate 
• 331766-99-5 (4S,5S)-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 

Downstream Products

• 144163-44-0 (2S,3S,5S)-3-hydroxy-2,5-bisamino-1,6-diphenylhexane 
• 144163-88-2 ((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

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

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.