75638-59-4

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3R)-3-Amino-2-hydroxyhexanoic acid is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique stereochemistry allows for the creation of enantiomerically pure drugs, which is essential for ensuring the desired biological activity and minimizing potential side effects.
Used in Organic Synthesis:
(2S,3R)-3-Amino-2-hydroxyhexanoic acid is used as a versatile intermediate in organic synthesis for the preparation of complex organic molecules. Its functional groups enable a range of reactions, such as amide bond formation, esterification, and other condensation reactions, making it a valuable component in the synthesis of natural products, agrochemicals, and other specialty chemicals.
Used in Research and Development:
(2S,3R)-3-Amino-2-hydroxyhexanoic acid is used as a research tool in the study of asymmetric synthesis, enzymatic reactions, and chiral recognition. Its unique stereochemistry provides insights into the mechanisms of enzyme-catalyzed reactions and the development of new chiral catalysts and reagents for asymmetric synthesis.

InChI:InChI=1/C6H13NO3/c1-2-3-4(7)5(8)6(9)10/h4-5,8H,2-3,7H2,1H3,(H,9,10)/t4-,5+/m1/s1

Upstream product

• 367258-42-2 2-hydroxy-3-nitrohexanoic acid 
• 117709-02-1 3-propylepoxyethane-2-carboxylic acid methyl ester 
• 13894-63-8 methyl (E)-hex-2-enoate 
• 608520-05-4 (3R,2S)-3-propyloxirane-2-carboxylic acid 
• 92418-71-8 (2R,3R)-2,3-epoxy-1-hexanol 
• 160801-73-0 (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamate 
• 160801-74-1 (2S)-2-(1,1-dimethylethoxycarbonylamino)pentanal 
• 53308-95-5 N-tert-butoxycarbonyl-L-norvaline 
• 364633-42-1 (3S)-3-tert-butoxycarbonylamino-2-hydroxyhexanenitrile 
• 154701-94-7 (2S,3R)-ethyl 2-hydroxy-3-(tosylamino)hexanoate 
• 154701-98-1 (2S,3R)-2-hydroxy-3-(tosylamino)hexanoic acid 

Relevant academic research and scientific papers

Synthesis method of alpha-hydroxyl-beta-amino acid simplex stereoscopic isomer

The invention relates to a synthesis method of an alpha-hydroxyl-beta-amino acid simplex stereoscopic isomer. The method mainly solves the technical problems that an existing synthesis method uses expensive chiral ligand or highly-toxic raw materials and is not suitable for industrial production. The method includes the steps of firstly, synthesizing substitutive alpha-hydroxyl-beta-amino acid despinner according to a literature method; secondly, stereoscopically and selectively synthesizing an alpha-hydroxyl-beta-amino acid simplex isomer of an (S,S) structure and an alpha-hydroxyl-beta-aminoacid simplex isomer of an (R,R) structure with penicillin G acylase. The method is suitable for preparing the alpha-hydroxyl-beta-amino acid simplex isomers efficiently at low cost.

Azetidines and spiro azetidines as novel P2 units in hepatitis C virus NS3 protease inhibitors

Herein, we report the synthesis and structure-activity relationship studies of new analogs of boceprevir 1 and telaprevir 2. Introduction of azetidine and spiroazetidines as a P2 substituent that replaced the pyrrolidine moiety of 1 and 2 led to the disco

Discovery of SCH446211 (SCH6): A new ketoamide inhibitor of the HCV NS3 serine protease and HCV subgenomic RNA replication

Introduction of various modified prolines at P2 and optimization of the P1 side chain led to the discovery of SCH6 (24, Table 2), a potent ketoamide inhibitor of the HCV NS3 serine protease. In addition to excellent enzyme potency (Ki* = 3.8 nM), 24 was also found to be a potent inhibitor of HCV subgenomic RNA replication with IC50 and IC90 of 40 and 100 nM, respectively. Recently, antiviral activity of 24 was demonstrated with inhibition of the full-length genotype 2a HCV genome. In addition, 24 was found to restore the responsiveness of the interferon regulatory factor 3 (IRF-3) in cells containing HCV RNA replicons.

Novel potent hepatitis C virus NS3 serine protease inhibitors derived from proline-based macrocycles

The hepatitis C virus (HCV) NS3 protease is essential for viral replication. It has been a target of choice for intensive drug discovery research. On the basis of an active pentapeptide inhibitor, 1, we envisioned that macrocyclization from the P2 proline

Potent 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid-based macrocyclic inhibitors of hepatitis C virus NS3 protease

The NS3 protease of hepatitis C virus (HCV) has emerged as one of the best characterized targets for next-generation HCV therapy. The tetrapeptide 1 and pentapeptide 2 are α-ketoamide-type HCV serine protease inhibitors with modest potency. We envisioned

Discovery of (1R,5S)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3- [2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6, 6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide (SCH 503034), a selective, potent, orally bioavailable hepatitis C virus NS3 protease inhibitor: A potential therapeutic agent for the treatment of hepatitis C infection

Hepatitis C virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, which affects more than 170 million people worldwide. Currently the only therapeutic regimens are subcutaneous interferon-α or polyethylene glycol (PEG)-interferon-α alone or in combination with oral ribavirin. Although combination therapy is reasonably successful with the majority of genotypes, its efficacy against the predominant genotype (genotype 1) is moderate at best, with only about 40% of the patients showing sustained virological response. Herein, the SAR leading to the discovery of 70 (SCH 503034), a novel, potent, selective, orally bioavailable NS3 protease inhibitor that has been advanced to clinical trials in human beings for the treatment of hepatitis C viral infections is described. X-ray structure of inhibitor 70 complexed with the NS3 protease and biological data are also discussed.

Design and synthesis of depeptidized macrocyclic inhibitors of hepatitis C NS3-4A protease using structure-based drug design

Hepatitus C virus (HCV) NS3, when bound to NS4A cofactor, facilitates development of mature virons by catalyzing cleavage of a polyprotein to form functional and structural proteins of HCV. The enzyme has a shallow binding pocket at the catalytic site, ma

NOVEL KETOAMIDES WITH CYCLIC P4'S AS INHIBITORS OF NS3 SERINE PROTEASE OF HEPATITIS C VIRUS

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

NOVEL COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

CYCLOBUTENEDIONE GROUPS-CONTAINING COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.