136465-89-9

Basic information

• Product Name: (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane
• Synonyms: (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane
• CAS NO: 136465-89-9
• Molecular Weight: 189.217
• Mol File: 136465-89-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane(136465-89-9)
• EPA Substance Registry System: (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane(136465-89-9)

Safety Data

• Hazardous Substances Data: 136465-89-9(Hazardous Substances Data)

Upstream product

• 116949-67-8 (2S,3S)-2-azido-1-phenyl-butane-3,4-diol 
• 136465-96-8 3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol 
• 54966-42-6 ethyl 3-benzylacrylate 
• 42238-15-3 (2E)-4-phenylbut-2-en-1-ol 
• 161170-92-9 (2S,3R)-2-Hydroxymethyl-3-phenylmethyloxirane 
• 78571-81-0 (R,R)-3-(phenylmethyl)oxiranemethanol 
• 78571-81-0 (3-benzyloxiran-2-yl)methanol 
• 85531-71-1 (3-benzyloxiran-2-yl)methanol 
• 122-78-1 phenylacetaldehyde 
• 140867-27-2 (2R,3R)-1,2-O-methylethylidene-4-phenylbutane-1,2,3-triol 

Downstream Products

• 136465-90-2 N-tert-butyl-2-<2(R)-hydroxy-4-phenyl-3(S)-azidobutyl>decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 162776-62-7 N-tert-butyl-2-<2(R)-hydroxy-4-phenyl-3(S)-azidobutyl>octahydro-(3S,4aS,7aS)-1H-pyrindene-3(S)-carboxamide 
• 206361-96-8 (2R,3R)-3-azido-4-phenylbutane-1,2-diol 
• 245523-39-1 N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide 
• 482358-74-7 (2R,3S)-3-Azido-1-but-3-enylamino-4-phenyl-butan-2-ol 
• 482358-73-6 (2R,3S)-1-Allylamino-3-azido-4-phenyl-butan-2-ol 
• 883976-32-7 (2R,3S)-3-Azido-1-(3-methyl-butylamino)-4-phenyl-butan-2-ol 
• 883976-33-8 (2R,3S)-3-Azido-1-benzylamino-4-phenyl-butan-2-ol 
• 883976-36-1 3-[((2R,3S)-3-Azido-2-hydroxy-4-phenyl-butyl)-(3-methyl-butyl)-amino]-3-methyl-1,3-dihydro-indol-2-one 
• 883976-34-9 (R)-3-[((2R,3S)-3-Azido-2-hydroxy-4-phenyl-butyl)-isobutyl-amino]-3-methyl-1,3-dihydro-indol-2-one 
• 883976-35-0 (S)-3-[((2R,3S)-3-Azido-2-hydroxy-4-phenyl-butyl)-isobutyl-amino]-3-methyl-1,3-dihydro-indol-2-one 
• 883976-64-5 3-[((2R,3S)-3-Azido-2-hydroxy-4-phenyl-butyl)-benzyl-amino]-3-methyl-1,3-dihydro-indol-2-one 
• 482358-77-0 Allyl-((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-carbamic acid dec-9-enyl ester 
• 482358-78-1 ((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-but-3-enyl-carbamic acid 1-phenyl-dec-9-enyl ester 

Relevant articles and documents

PROCESS FOR SYNTHESIS OF SYN AZIDO EPOXIDE AND ITS USE AS INTERMEDIATE FOR THE SYNTHESIS OF AMPRENAVIR and SAQUINAVIR

Disclosed herein is a novel route of synthesis of syn azide epoxide of formula 5, which is used as a common intermediate for asymmetric synthesis of HIV protease inhibitors such as Amprenavir, Fosamprenavir, Saquinavir and formal synthesis of Darunavir an

Enantioselective synthesis of HIV protease inhibitor amprenavir via Co-catalyzed HKR of 2-(1-azido-2-phenylethyl)oxirane

A short and efficient enantioselective synthesis of the HIV protease inhibitor amprenavir 1 (99% ee) as well as a formal synthesis of saquinavir 3 have been achieved in high enantiomeric purity starting from commercially available materials. Our strategy mainly comprises a Co-catalyzed two-stereocentred hydrolytic kinetic resolution (HKR) of racemic 2-(1-azido-2-phenylethyl)oxirane as the chirality inducing step. Also presented is a concise synthesis of (S)-3-hydroxytetrahydrofuran 4, the key structural feature, in high enantiomeric purity (98% ee).

FITNESS ASSAY AND ASSOCIATED METHODS

The present invention provides an assay for determining the biochemical fitness of a biochemical species in a mutant replicating biological entity relative to its predecessor. The present invention further provides a continuous fluorogenic assay for measuring the anti-HIV protease activity of protease inhibitor. The present invention also provides a method of administering a therapeutic compound that reduces the chances of the emergence of drug resistance in therapy. The present invention also provides a compound of formula (I) or a pharmaceutically acceptable salt, a prodrug, a composition, or an ester thereof, wherein A is a group of formulas (A), (B), (C) or (D); R1, R2, R3, R5 or R6 is H, or an optionally substituted and/or heteroatom-bearing alkyl, alkenyl, alkynyl, or cyclic group; Y and/or Z are CH2, O, S, SO, SO2, amino, amides, carbamates, ureas, or thiocarbonyl derivatives thereof, optionally substituted with an alkyl, alkenyl, or alkynyl group; n is from 1 to 5; X is a bond, an optionally substituted methylene or ethylene, an amino, O or S; Q is C(O), C(S), or SO2; m is from 0 to 6; R4 is OH, ═O (keto), NH2, or alkylamino, including esters, amides, and salts thereof; and W is C(O), C(S), S(O), or SO2. Optionally, R5 and R6, together with the N—W bond of formula (I), comprise a macrocyclic ring.