128018-44-0

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane is used as a key building block in the synthesis of pharmaceuticals for its ability to be selectively transformed into more complex organic molecules. The Cbz group protects the amine function, allowing for other functional groups to be modified without affecting the amine, which is crucial for the synthesis of specific drug candidates.
Used in Organic Chemistry Research:
In the field of organic chemistry, (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane serves as a valuable intermediate for studying the reactivity of epoxy groups and the effects of the Cbz protecting group on amine chemistry. Its use in research helps to advance the understanding of reaction mechanisms and the development of new synthetic methodologies.
Used in the Production of Biologically Active Compounds:
(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane is utilized as a precursor in the production of biologically active compounds, leveraging its reactive epoxy group for ring-opening reactions that can lead to the formation of diverse molecular structures with potential biological activity.
Used in Chiral Synthesis:
As a chiral molecule with non-superimposable mirror images, (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane is employed in chiral synthesis to produce enantiomerically pure compounds. This is particularly important in pharmaceutical development, where the stereochemistry of a molecule can significantly affect its efficacy and safety.

InChI:InChI=1/C18H19NO3/c20-18(22-12-15-9-5-2-6-10-15)19-16(17-13-21-17)11-14-7-3-1-4-8-14/h1-10,16-17H,11-13H2,(H,19,20)/t16-,17?/m0/s1

Upstream product

• 19317-12-5 (3S)-3-(N-benzyloxycarbonylamino)-3-benzyl-2-oxo-1-bromopropane 
• 116949-67-8 (2S,3S)-2-azido-1-phenyl-butane-3,4-diol 
• 1161-13-3 N-Cbz-L-Phe 
• 41518-17-6 Z-Phe-O-COO-isoBu 
• 128018-43-9 N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol 
• 186463-41-2 2(R,S)-3(S)-1-chloro-2-hydroxy-3-phenylmethoxycarbonylamino-4-phenylbutane 
• 165187-29-1 N-benzyloxycarbonyl-3(S)-amino-2(R)-methanesulfonyloxy-4-phenyl-1-butanol 
• 165187-27-9 N-benzyloxycarbonyl-3(S)-amino-2(R)-p-toluenesulfonyloxy-4-phenyl-1-butanol 
• 62023-59-0 (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 15196-02-8 (S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone 
• 147915-02-4 (2S,3S)-3-amino-4-phenylbutane-1,2-diol 
• 78571-81-0 (R,R)-3-(phenylmethyl)oxiranemethanol 
• 26049-94-5 (S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 164394-36-9 (2S,3S)-3-(benzyloxycarbonylamino)-4-phenylbutane-1,2-diol 

Downstream Products

• 1055030-54-0 {(1S,2R)-1-Benzyl-2-hydroxy-3-[(pyridin-4-ylmethyl)-amino]-propyl}-carbamic acid benzyl ester 
• 184357-24-2 [(1S,2R)-1-Benzyl-3-(cyclohexylmethyl-amino)-2-hydroxy-propyl]-carbamic acid benzyl ester 
• 260562-76-3 Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid benzyl ester 
• 143224-78-6 C₂₆H₃₀N₂O₄ 
• 1053733-49-5 C₂₅H₂₇FN₂O₃ 
• 1053557-51-9 C₂₄H₃₂N₂O₃ 
• 143224-69-5 C₂₉H₃₀N₂O₃ 
• 1054635-60-7 C₂₁H₂₈N₂O₃ 
• 143224-72-0 C₂₆H₃₀N₂O₃ 
• 857904-42-8 Tert-butyl 2-((2S,3S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutyl)-2-(4-nitrobenzyl)hydrazinecarboxylate 
• 191850-79-0 C₂₈H₃₉N₃O₇ 
• 1057253-52-7 C₂₈H₃₉N₃O₅ 
• 191851-41-9 C₃₀H₄₁N₃O₆ 

Relevant academic research and scientific papers

Design, biologic evaluation, and SAR of novel pseudo-peptide incorporating benzheterocycles as HIV-1 protease inhibitors

A series of novel HIV-1 protease inhibitors based on the (hydroxyethylamino)-sulfonamide isostere incorporating substituted phenyls and benzheterocycle derivatives bearing rich hydrogen bonding acceptors as P 2 ligands were synthesized. Prolonged chain linking the benzhereocycle to the carbonyl group resulted in partial loss of binding affinities. Introduction of a small alkyl substituent with appropriate size to the -CH2- of P1-P2 linkage as a side chain resulted in improved inhibitory potency, and in this study, isopropyl was the best side chain. Replacement of the isobutyl substituent at P 1′group with phenyl substituent decreased the inhibitory potency. One of the most potent inhibitor, compound 23 showing high affinity to HIV-1 protease with an IC50 value of 5 nm, also exhibited good anti-SIV activity (EC50 = 0.8 μm) with low toxicity (TC 50 > 100 μm). The flexible docking of inhibitor 23 to HIV-1 protease active site rationalized the interactions with protease.

Highly diastereoselective catalytic Meerwein-Ponndorf-Verley reductions

Very practical synthesis of ephedrine analogues in high yields and enantiopurity was realized by a highly diastereoselective Meerwein-Ponndorf- Verley (MPV) reduction of protected α-amino aromatic ketones using catalytic aluminum isopropoxide. The high anti selectivity resulted from the chelation of the nitrogen anion to the aluminum. In contrast, high syn selectivity was obtained with α-alkoxy ketones and other compounds via Felkin-Ahn control.

HIV protease inhibitors

Combinatorial libraries of HIV and FIV protease inhibitors are characterized by alpha-keto amide or hydroxyethylamine core structures flanked by on one side by substituted pyrrolidines, piperidines, or azasugars and on the other side by phenylalanine, tyrosine, or substituted tyrosines. The libraries are synthesized via a one step coupling reaction. Highly efficacious drug candidates are identified by screening the libraries for binding and inhibitory activity against both HIV and FIV protease. Drug candidates displaying clinically useful activity against both HIV and FIV protease are identified as being potentially resistive against a loss of inhibitory activity due to development of resistant strains of HIV.

New approaches to the industrial synthesis of HIV protease inhibitors

Efficient and industrially applicable synthetic processes for precursors of HIV protease inhibitors (Amprenavir, Fosamprenavir) are described. These involve a novel and economical method for the preparation of a key intermediate, (3S)-hydroxytetrahydrofuran, from L-malic acid. Three new approaches to the assembly of Amprenavir are also discussed. Of these, a synthetic route in which an (S)-tetrahydrofuranyloxy carbonyl is attached to L-phenylalanine appears to be the most promising manufacturing process, in that it offers satisfactory stereoselectivity in fewer steps.

Retroviral protease inhibitors

N-heterocyclic moiety-containing hydroxyethylamine protease inhibitor compounds, methods for making the compounds, and intermediates useful in the method. Also, a method for inhibiting retroviral proteases and for treatment or prophylaxis of a retroviral infection.

α-and β-amino acid hydroxyethlamino sulfonamides useful as retroviral protease inhibitors

α- and β-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.

Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors

Selected bis-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.

Succinoylamino hydroxyethylamino sulfonyl urea derivatives useful as retroviral protease inhibitors

Succinoylamino hydroxyethylamino sulfonyl urea derivatives of the formula: wherein the substituents are as defined in the specification, are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.

HETEROCYCLECARBONYL AMINO ACID HYDROXYETHYLAMINO SULFONAMIDE RETROVIRAL PROTEASE INHIBITORS

Selected heterocyclecarbonyl amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.

Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors

PCT No. PCT/US94/09139 Sec. 371 Date Jan. 24, 1996 Sec. 102(e) Date Jan. 24, 1996 PCT Filed Aug. 23, 1994 PCT Pub. No. WO95/06030 PCT Pub. Date Mar. 2, 1995The invention relates to sulfonamide-containing hydroxyethylamine protease inhibitor compounds, their process of making, composition and method of use for inhibiting retroviral proteases such as human immunodeficiency virus.