128018-43-9

Basic information

• Product Name: (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane
• Synonyms: (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane;Benzyl (2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-ylcarbamate
• CAS NO: 128018-43-9
• Molecular Formula: C₁₈H₂₀ClNO₃
• Molecular Weight: 333.8093
• Mol File: 128018-43-9.mol
• Article Data: 45

Chemical Properties

• Boiling Point: 535.079 °C at 760 mmHg
• Flash Point: 277.406 °C
• Appearance: /
• Density: 1.232g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane(128018-43-9)
• EPA Substance Registry System: (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane(128018-43-9)

Safety Data

• Hazardous Substances Data: 128018-43-9(Hazardous Substances Data)

Usage

General Description

"(2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane" is a complex organic compound with both hydrophilic (water-loving) and hydrophobic (fat-loving) properties. The structure includes a chloro component (1-chloro), a hydroxy group (2-hydroxy), an amino group contained within a benzyloxycarbonyl unit, and a phenyl group. The "2S,3S" indicates the stereoisomerism of the molecule, specifically the spatial arrangement of the atoms which can impact the chemical's interactions with other substances. Typically, this type of compound could be used in chemical synthesis or in the development of pharmaceuticals, although without specific context, it's hard to identify its exact use.

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 
• 41518-17-6 Z-Phe-O-COO-isoBu 
• 1161-13-3 N-Cbz-L-Phe 
• 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 
• 191226-90-1 tert-butyl (4S)-4-N-benzyloxycarbonylamino-2-chloro-3-oxo-5-phenylpentanoate 
• 15196-02-8 (S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone 

Downstream Products

• 128018-44-0 N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane 
• 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 
• 143224-65-1 {(S)-1-[(1S,2R)-1-Benzyl-3-(3-tert-butyl-1-isobutyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester 
• 1053691-34-1 {(1S,2R)-1-Benzyl-3-[3-tert-butyl-1-((S)-1-phenyl-ethyl)-ureido]-2-hydroxy-propyl}-carbamic acid benzyl ester 
• 143224-66-2 (S)-2-Amino-N¹-[(1S,2R)-1-benzyl-3-(3-tert-butyl-1-isobutyl-ureido)-2-hydroxy-propyl]-succinamide 
• 1053647-75-8 1-((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-3-tert-butyl-1-((S)-1-phenyl-ethyl)-urea 
• 1053702-87-6 1-((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-3-butyl-1-methyl-urea 

Relevant articles and documents

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.

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.

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.