78571-81-0

Basic information

• Product Name: 2-Hydroxymethyl-3-phenylmethyloxirane
• CAS NO: 78571-81-0
• Molecular Weight: 164.204
• Mol File: 78571-81-0.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 2-Hydroxymethyl-3-phenylmethyloxirane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxymethyl-3-phenylmethyloxirane(78571-81-0)
• EPA Substance Registry System: 2-Hydroxymethyl-3-phenylmethyloxirane(78571-81-0)

Safety Data

• Hazardous Substances Data: 78571-81-0(Hazardous Substances Data)

Upstream product

• 122-78-1 phenylacetaldehyde 
• 54966-42-6 ethyl 3-benzylacrylate 
• 22910-59-4 (Z)-4-phenylbut-2-en-1-ol 
• 42238-15-3 (2E)-4-phenylbut-2-en-1-ol 
• 54966-42-6 ethyl 4-phenylbut-2-enoate 
• 559062-83-8 ethyl (2Z)-4-phenyl-2-butenoate 

Downstream Products

• 219607-70-2 (2S,3S)-2,3-epoxy-1-(4-methoxybenzyl)oxy-4-phenylbutane 
• 151250-78-1 Benzoic acid (2S,3S)-3-azido-2-hydroxy-4-phenyl-butyl ester 
• 140867-26-1 2(R)-<1'(S)-azido-2'-phenylethyl>oxirane 
• 136465-96-8 3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol 
• 1381874-40-3 C₁₀H₁₁ClO 
• 6052-66-0 (S)-(+)-1-phenylbut-3-en-2-ol 
• 1381874-36-7 C₁₀H₁₁ClO 
• 151636-81-6 (2R)-1-phenylbut-3-en-2-ol 
• 1394027-30-5 (2R,3R)-3-azido-4-phenylbutane-1,2-diol 
• 136465-89-9 (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane 
• 136465-90-2 N-tert-butyl-2-<2(R)-hydroxy-4-phenyl-3(S)-azidobutyl>decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 206361-96-8 (2R,3R)-3-azido-4-phenylbutane-1,2-diol 
• 161814-49-9 amprenavir 
• 251105-80-3 N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride 

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.