81096-89-1

Upstream product

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

Downstream Products

• 219607-70-2 (2S,3S)-2,3-epoxy-1-(4-methoxybenzyl)oxy-4-phenylbutane 
• 1042267-84-4 methanesulfonic acid (2S,3S)-2,3-epoxy-4-phenylbutyl ester 
• 1381874-40-3 C₁₀H₁₁ClO 
• 6052-66-0 (S)-(+)-1-phenylbut-3-en-2-ol 
• 78571-83-2 (2R,3S)-3-Benzyl-oxirane-2-carboxylic acid 
• 1014685-43-8 methanesulfonic acid (2R,3R)-2,3-epoxy-4-phenylbutyl ester 
• 1381874-36-7 C₁₀H₁₁ClO 
• 151636-81-6 (2R)-1-phenylbut-3-en-2-ol 
• 5445-77-2 2-benzylpropionaldehyde 
• 2439-43-2 (2RS)-2-phenylbutanal 
• 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 

Relevant academic research and scientific papers

A pH Study on the Chiral Ketone Catalyzed Asymmetric Epoxidation of Hydroxyalkenes

A detailed study shows that the chiral ketone catalyzed asymmetric epoxidations of hydroxyalkenes are highly pH dependent. The lower enantioselectivity obtained at low pH is attributed to the substantial contribution of the direct epoxidation by Oxone. At high pH the epoxidation mediated by chiral ketone out-competes the racemic epoxidation, leading to higher enantioselectivity. The effective substrates include allylic alcohol, homoallylic alcohol, and bishomoallylic alcohol. In most cases, over 90% ee was obtained.

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

Dynamic kinetic asymmetric transformations of β-stereogenic α-ketoesters by direct aldolization

Dynamic kinetic asymmetric transformations (DyKAT) of racemic β-bromo-α-keto esters by direct aldolization of nitromethane and acetone provide access to fully substituted α-glycolic acid derivatives bearing a β-stereocenter. The aldol adducts are obtained

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).

Stereoselective synthesis of alpinoid-C and its analogues and study of their cytotoxic activity against cancer cell lines

A simple, highly efficient and stereoselective synthetic route has been developed for synthesis of alpinoid-C (1) and its analogues (2, 3 and 4) from commercially available starting materials by using Wittig olefination, Sharpless asymmetric epoxidation,

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.

Synthesis and evaluation of novel pyrazolidinone analogs of PGE2 as EP2 and EP4 receptors agonists

Replacement of the hydroxy cyclopentanone ring in PGE2 with chemically more stable heterocyclic rings and substitution of the unsaturated α-alkenyl chain with a metabolically more stable phenethyl chain led to the development of potent and selective analogs of PGE2. Compound 10f showed the highest potency and selectivity for EP4 the receptor.

Enantiodivergent, catalytic asymmetric synthesis of γ-amino vinyl sulfones

A set of diversely substituted N-Boc-γ-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of α-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given γ-amino vinyl sulfone can be obtained with equal ease.

First one-pot copper-catalyzed synthesis of α-hydroxy-β-amino acids in water. A new protocol for preparation of optically active norstatines

α-Hydroxy-β-amino acids were synthesized with excellent yields for the first time in water and by a simple procedure based on a copper catalytic cycle, which included the recovery and reuse of the catalyst and is possible to realize by using only water as reaction medium.

Base promoted isomerization of aziridinyl ethers: a new access to alpha- and beta-amino acids.

Aziridinyl ethers are selectively and easily converted to either amino vinyl ethers or alkoxy allylamines by treatment with mixed metal bases (superbases).