206361-96-8

Basic information

• Product Name: (2R,3R)-3-azido-4-phenylbutane-1,2-diol
• Synonyms: (2R,3R)-3-azido-4-phenylbutane-1,2-diol
• CAS NO: 206361-96-8
• Molecular Weight: 262.355
• Mol File: 206361-96-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2R,3R)-3-azido-4-phenylbutane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-3-azido-4-phenylbutane-1,2-diol(206361-96-8)
• EPA Substance Registry System: (2R,3R)-3-azido-4-phenylbutane-1,2-diol(206361-96-8)

Safety Data

• Hazardous Substances Data: 206361-96-8(Hazardous Substances Data)

Upstream product

• 78-81-9 isobutylamine 
• 136465-89-9 (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane 
• 54966-42-6 ethyl 3-benzylacrylate 
• 42238-15-3 (2E)-4-phenylbut-2-en-1-ol 
• 78571-81-0 (3-benzyloxiran-2-yl)methanol 
• 85531-71-1 (3-benzyloxiran-2-yl)methanol 

Downstream Products

• 253265-96-2 N-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-methoxybenzenesulfonamide 
• 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 
• 206362-03-0 N-((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-N-isobutyl-4-methyl-benzenesulfonamide 
• 169280-56-2 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide 
• 161814-49-9 amprenavir 
• 206361-99-1 darunavir 
• 160231-69-6 4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide 
• 1348180-72-2 amprenavir 
• 473739-27-4 2-Methylsulfanyl-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide 
• 473739-21-8 {(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(2-methylsulfanyl-benzothiazole-6-sulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester 
• 951207-65-1 (2R,3S)-3-azido-2-hydroxy-1-[N-isobutylamino-N'-[(3-tetrahydropyranoxy)-benzenesulfonamidoyl]]-4-phenylbutane 

Relevant articles and documents

Design and Development of Highly Potent HIV-1 Protease Inhibitors with a Crown-Like Oxotricyclic Core as the P2-Ligand To Combat Multidrug-Resistant HIV Variants

Design, synthesis, and evaluation of a new class of exceptionally potent HIV-1 protease inhibitors are reported. Inhibitor 5 displayed superior antiviral activity and drug-resistance profiles. In fact, this inhibitor showed several orders of magnitude improved antiviral activity over the FDA approved drug darunavir. This inhibitor incorporates an unprecedented 6-5-5 ring-fused crown-like tetrahydropyranofuran as the P2 ligand and an aminobenzothiazole as the P2′ ligand with the (R)-hydroxyethylsulfonamide isostere. The crown-like P2 ligand for this inhibitor has been synthesized efficiently in an optically active form using a chiral Diels-Alder catalyst providing a key intermediate in high enantiomeric purity. Two high resolution X-ray structures of inhibitor-bound HIV-1 protease revealed extensive interactions with the backbone atoms of HIV-1 protease and provided molecular insight into the binding properties of these new inhibitors.

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

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

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.