128018-43-9

Usage

Uses

Used in Chemical Synthesis:
(2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane is used as an intermediate in chemical synthesis for its unique structural features, including the chloro, hydroxy, and amino groups, which can be manipulated to form a variety of other compounds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane is used as a potential building block for the creation of new drugs. Its stereochemistry and functional groups may contribute to the development of molecules with specific biological activities, such as targeting certain receptors or enzymes in the body.

InChI:InChI=1/C18H20ClNO3/c19-12-17(21)16(11-14-7-3-1-4-8-14)20-18(22)23-13-15-9-5-2-6-10-15/h1-10,16-17,21H,11-13H2,(H,20,22)/t16-,17+/m0/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 15196-02-8 (S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone 
• 1161-13-3 N-Cbz-L-Phe 
• 41518-17-6 Z-Phe-O-COO-isoBu 
• 191226-90-1 tert-butyl (4S)-4-N-benzyloxycarbonylamino-2-chloro-3-oxo-5-phenylpentanoate 
• 143601-45-0 (S)-tert-butyl 4-<(benzyloxycarbonyl)amino>-3-oxo-5-phenylpentanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 26049-94-5 (S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 

Downstream Products

• 160232-67-7 (2S,3S)-3-Amino-1-chloro-4-phenyl-butan-2-ol 
• 128018-44-0 N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane 
• 128053-39-4 (S)-1-((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-pyrrolidine-2-carboxylic acid tert-butylamide 
• 128018-20-2 N-<1-phenyl-2(S)-<(benzyloxycarbonyl)amino>-3(R)-hydroxybutan>-4-L-prolyl-tert-butyl amide 
• 160232-13-3 (2R,3S)-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-2-hydroxy-1-N-(isobutyl)amino-4-phenylbutane 
• 160232-69-9 (2S,3S)-1-chloro-2-hydroxy-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-4-phenylbutane 
• 160231-69-6 4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide 
• 160232-70-2 (1S,1'S)-1-(1'-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-2'-phenyl)ethyloxirane 
• 127231-61-2 C₄₉H₇₄N₈O₁₁ 
• 127306-15-4 JG₃₆₅ (R isomer) 
• 132234-32-3 (S)-2-[(2S,3S)-2-({(S)-1-[(2R,3S)-3-((S)-2-tert-Butoxycarbonylamino-3-carbamoyl-propionylamino)-2-hydroxy-4-phenyl-butyl]-pyrrolidine-2-carbonyl}-amino)-3-methyl-pentanoylamino]-3-methyl-butyric acid methyl ester 
• 132234-33-4 (S)-2-((2S,3S)-2-{[(S)-1-((2R,3S)-3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoylamino)-3-methyl-butyric acid methyl ester 
• 148245-96-9 {(S)-1-[(1S,2R)-1-Benzyl-3-(3-butyl-1-isobutyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester 
• 143224-34-4 Telinavir 

Relevant academic research and scientific papers

Synthetic method of HIV protease inhibitor intermediate compound

The invention is suitable for the technical field of drug synthesis, and provides a synthesis method of an HIV protease inhibitor intermediate compound. The method comprises the following steps: underthe protection of argon, adding a catalyst and hydrogen source mixture into a compound 1a in a reaction solvent, and carrying out asymmetric transfer hydrogenation reaction to obtain the HIV proteaseinhibitor intermediate compound 2a or 2a'. The synthetic route is shown as follows: the group R is one of tert-butyloxycarboryl, carbobenzoxy, p-toluenesulfonyl, acetyl and benzoyl. The asymmetric transfer hydrogenation technology is utilized, compared with existing similar intermediates, the stereoselectivity and yield of the synthesized HIV protease inhibitor intermediate compound can be greatly improved, and the diastereoselectivity ratio of the product reaches 94:6; and in addition, the catalyst is low in dosage and high in catalytic efficiency, reaction activity is improved, raw materialloss is low, the whole process is rapid, simple and convenient, and cost is greatly reduced.

Rh(iii)-Catalyzed diastereoselective transfer hydrogenation: An efficient entry to key intermediates of HIV protease inhibitors

A highly efficient diastereoselective transfer hydrogenation of α-aminoalkyl α′-chloromethyl ketones catalyzed by a tethered rhodium complex was developed and successfully utilized in the synthesis of the key intermediates of HIV protease inhibitors. With the current Rh(iii) catalyst system, a series of chiral 3-amino-1-chloro-2-hydroxy-4-phenylbutanes were produced in excellent yields and diastereoselectivities (up to 99% yield, up to 99?:?1 dr). Both diastereomers of the desired products could be efficiently accessed by using the two enantiomers of the Rh(iii) catalyst.

Chiral chlorohydrins from the biocatalyzed reduction of chloroketones: Chiral building blocks for antiretroviral drugs

E. coli cells that contain overexpressed alcohol dehydrogenases (ADHs) were screened as biocatalysts for the stereoselective reduction of chloroketones 5 a-d, the corresponding halohydrins 6 a-d of which are building blocks in the synthesis of antiretroviral drugs. Among them, ADH from Sphingobium yanoikuyae was found to reduce chloroketone 5 c with a high stereoselectivity (90 % de) and conversion (85 %) to furnish threo halohydrin (R,S)-6 c. ADH from Ralstonia sp. (RasADH) was able to reduce 5 a and 5 b with complementary diastereoselectivity to provide access to both threo and erythro halohydrins through "substrate-based" stereocontrol. The RasADH-catalyzed reductions were optimized to provide (R,S)-6 a with 98 % conversion and 84 % diastereomeric excess (de) and (S,S)-6 b with 95 % conversion and 86 % de. Molecular modeling studies showed that 5 b, which features a carboxybenzyl protecting group, is able to bind to the enzyme catalytic site in an "inverted" mode in comparison to tert-butyloxycarbonyl- and methyloxycarbonyl-protected substrates 5 a and 5 c, which sheds light on the observed switching of the stereopreference. RasADH-catalyzed reductions were optimized to provide (R,S)-6 a with 98 % conversion and 84 % de and (S,S)-6 b with 95 % conversion and 86 % de.

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.

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.

Self-emulsifying drug delivery system

Oral pharmaceutical formulation which improves the bioavailability of pharmaceuticals which are substantially water and oil insoluble is disclosed. In addition to the pharmaceutical, the formulation includes an emulsifier, an oil and an solubilizer. Alter

Asymmetric transfer hydrogenation of α-aminoalkyl α′-chloromethyl ketones with chiral Rh complexes

Asymmetric transfer hydrogenation of N-substituted (3S)-3-amino-1-chloro-4- phenyl-2-butanones in the presence of Cp*RhCl[(R,R)-Tsdpen] (S/C = 1000) with a mixture of formic acid/triethylamine gave N-substituted (2R,3S)-3-amino-1-chloro-2-hydroxy-4-phenylbutanes with up to 93% de in a quantitative yield, and reduction with the enantiomeric catalyst Cp*RhCl[(S,S)-Tsdpen] gave (2S.3S)-diastereomeric alcohol with up to 96% de.

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.

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.