75638-59-4

Basic information

• Product Name: (2S,3R)-3-AMINO-2-HYDROXYHEXANOIC ACID
• Synonyms: (2S,3R)-3-AMINO-2-HYDROXYHEXANOIC ACID
• CAS NO: 75638-59-4
• Molecular Formula: C6H13NO3
• Molecular Weight: 147.17232
• Product Categories: API intermediates
• Mol File: 75638-59-4.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• Refractive Index: 1.498
• CAS DataBase Reference: (2S,3R)-3-AMINO-2-HYDROXYHEXANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-3-AMINO-2-HYDROXYHEXANOIC ACID(75638-59-4)
• EPA Substance Registry System: (2S,3R)-3-AMINO-2-HYDROXYHEXANOIC ACID(75638-59-4)

Safety Data

• Hazardous Substances Data: 75638-59-4(Hazardous Substances Data)

Usage

Description

(2S,3R)-3-Amino-2-hydroxyhexanoic acid is a chiral amino acid with specific stereochemistry, featuring a 3-amino and 2-hydroxy functional group arrangement. It is characterized by its 2S,3R configuration, which is crucial for its reactivity and selectivity in chemical reactions.

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

• 154701-98-1 (2S,3R)-2-hydroxy-3-(tosylamino)hexanoic 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 
• 367258-42-2 2-hydroxy-3-nitrohexanoic acid 
• 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 

Relevant articles and documents

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.

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.

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