(2S,3S)-3-Amino-2-hydroxyhexanoic acid

Base Information

• Chemical Name: (2S,3S)-3-Amino-2-hydroxyhexanoic acid
• CAS No.: 160801-76-3
• Molecular Formula: C₆H₁₃NO₃
• Molecular Weight: 147.174
• DSSTox Substance ID: DTXSID80458626
• Nikkaji Number: J1.947.829G
• Wikidata: Q72437818
• Mol file: 160801-76-3.mol

Synonyms:(2S,3S)-3-AMINO-2-HYDROXYHEXANOIC ACID;160801-76-3;Hexanoic acid, 3-amino-2-hydroxy-, (2S,3S)-;(2S,3S)-3-AMINO-2-HYDROXYHEXANOICACID;SCHEMBL15609874;DTXSID80458626;(2S,3S)-2-Hydroxy-3-aminohexanoic acid

Chemical Property of (2S,3S)-3-Amino-2-hydroxyhexanoic acid

Chemical Property:

• Vapor Pressure: 7.39E-06mmHg at 25°C
• Refractive Index: 1.498
• Boiling Point: 337 °C at 760 mmHg
• Flash Point: 157.6 °C
• PSA: 83.55000
• Density: 1.185 g/cm³
• LogP: 0.25960
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

98%min ^*data from raw suppliers

(2S,3S)-3-AMINO-2-HYDROXYHEXANOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C(C(=O)O)O)N
• Isomeric SMILES: CCC[C@@H]([C@@H](C(=O)O)O)N

Technology Process of (2S,3S)-3-Amino-2-hydroxyhexanoic acid

There total 14 articles about (2S,3S)-3-Amino-2-hydroxyhexanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

β-azido-α-hydroxyhexanoic acid → 2-hydroxy-3-aminohexanoic acid (160801-75-2,160801-76-3,75638-60-7,75638-59-4)

Guidance literature:

With sodium tetrahydroborate; copper(II) nitrate; In water; at 0 ℃; for 0.5h;

DOI:10.1021/jo034752y

Reference yield: 66.0%

2-hydroxy-3-nitrohexanoic acid (367258-42-2) → 3-amino-2-hydroxyhexanoic acid (166196-05-0,160801-76-3,160801-75-2,75638-60-7,75638-59-4)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; under 3051.17 - 3102.89 Torr;

DOI:10.1021/jm0489556 DOI:10.1021/jm060077j

Reference yield:

(2R,3R)-2,3-epoxy-1-hexanol (92418-71-8) → (-)-(2S,3S)-3-amino-2-hydroxyhexanoic acid (160801-75-2,160801-76-3,75638-60-7,75638-59-4)

Guidance literature:

Multi-step reaction with 3 steps

1: periodic acid; RuCl₃

2: NaN₃ / Cu(NO₃)2 / H₂O / 1.5 h / 65 °C / pH 4.3 - 5.5

3: NaBH₄ / Cu(NO₃)2 / H₂O / 0.5 h / 0 °C

With ruthenium trichloride; sodium tetrahydroborate; sodium azide; periodic acid; copper(II) nitrate; In water; 1: Sharpless oxidation;

DOI:10.1021/jo034752y

upstream raw materials:

(3S)-3-tert-butoxycarbonylamino-2-hydroxyhexanenitrile

N-tert-butoxycarbonyl-L-norvaline

(2S)-2-(1,1-dimethylethoxycarbonylamino)pentanal

(S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamate

Downstream raw materials:

(3S)-3-(tert-butoxycarbonylamino)-2-hydroxyhexanoic acid

N-cyclopropyl-3-amino-2-hydroxyhexanamide hydrochloride

Refernces

• 1、 Bondada, Lavanya,Rondla, Ramu,Pradere, Ugo,Liu, Peng,Li, Chengwei,Bobeck, Drew,McBrayer, Tamara,Tharnish, Philip,Courcambeck, Jerome,Halfon, Philippe,Whitaker, Tony,Amblard, Franck,Coats, Steven J.,Schinazi, Raymond F.. "Azetidines and spiro azetidines as novel P2 units in hepatitis C virus NS3 protease inhibitors". . p. 6325 - 6330. Retrieved 2013/11/19.
• 2、 Chen, Kevin X.,Njoroge, F. George,Arasappan, Ashok,Venkatraman, Srikanth,Vibulbhan, Bancha,Yang, Weiying,Parekh, Tejal N.,Pichardo, John,Prongay, Andrew,Cheng, Kuo-Chi,Butkiewicz, Nancy,Yao, Nanhua,Madison, Vincent,Girijavallabhan, Viyyoor. "Novel potent hepatitis C virus NS3 serine protease inhibitors derived from proline-based macrocycles". . p. 995 - 1005. Retrieved 2007/10/03.