(S)-2-Amino-6-hydroxyhexanoic acid

Base Information

• Chemical Name: (S)-2-Amino-6-hydroxyhexanoic acid
• CAS No.: 6033-32-5
• Molecular Formula: C6H13 N O3
• Molecular Weight: 147.174
• Hs Code.: 2922509090
• UNII: 874D12O72W
• Nikkaji Number: J977.779B
• Wikidata: Q27096308
• ChEMBL ID: CHEMBL1233976
• Mol file: 6033-32-5.mol

Synonyms:2-amino-6-hydroxycaproic acid;6-hydroxy-2-aminocaproic acid;alpha-amino-epsilon-hydroxycaproic acid;epsilon-hydroxynorleucine;epsilon-hydroxynorleucine, (DL)-isomer;epsilon-hydroxynorleucine, (L)-isomer;HACA cpd

Chemical Property of (S)-2-Amino-6-hydroxyhexanoic acid

Chemical Property:

• Melting Point: 238-241°C
• Boiling Point: 361.7°Cat760mmHg
• Flash Point: 172.6°C
• PSA: 83.55000
• Density: 1.189g/cm³
• LogP: 0.26120
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly, Sonicated), Water (Slightly)
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 105

Purity/Quality:

99% ^*data from raw suppliers

L-6-Hydroxy norleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCO)CC(C(=O)O)N
• Isomeric SMILES: C(CCO)C[C@@H](C(=O)O)N
• Uses: A key chiral intermediate used for synthesis of a vasopeptidase inhibitor. L-6-HYDROXYNORLEUCINE is a key chiral intermediate used for synthesis of a vasopeptidase inhibitor

Technology Process of (S)-2-Amino-6-hydroxyhexanoic acid

There total 44 articles about (S)-2-Amino-6-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: 95.0%

(S)-2-(((benzyloxy)carbonyl)amino)-6-hydroxyhexanoic acid (102922-72-5) → (S)-2-amino-6-hydroxyhexanoic acid (6033-32-5)

Guidance literature:

With 10% Pd/C; hydrogen; In methanol; water;

DOI:10.1134/S1068162008060034

Reference yield: 92.0%

L-N-benzyloxycarbonyl-ε-hydroxynorleucine → (S)-2-amino-6-hydroxyhexanoic acid (6033-32-5)

Guidance literature:

With hydrogen; 10% palladium on activated carbon; In methanol; at 20 ℃; under 760.051 Torr;

Reference yield: 80.0%

ethyl 6-(tert-butyldimethylsilyloxy)-2-oxohexanoate (253437-61-5) → (S)-2-amino-6-hydroxyhexanoic acid (6033-32-5)

Guidance literature:

ethyl 6-(tert-butyldimethylsilyloxy)-2-oxohexanoate; With sodium hydroxide; potassium hydrogensulfate; In methanol; at 0 - 2 ℃; for 0.333333h; pH=7.15;

With sodium hydroxide; potassium hydrogensulfate; In acetonitrile; at 20 ℃; for 1h;

With glucose dehydrogenase; beef liver glutamate dehydrogenase; NAD; In water; at 30 ℃; for 25h; pH=8.75; Enzymatic reaction;

DOI:10.1016/S0968-0896(99)00158-3

upstream raw materials:

rac-6-hydroxynorleucine

L-lysine

5-(4-hydroxybutyl)hydantoin

2-((S)-2-Oxo-oxepan-3-yl)-isoindole-1,3-dione

Downstream raw materials:

(S)-2-((tert-butoxycarbonyl)amino)-6-hydroxyhexanoic acid

N^α-(tert-butyloxycarbonyl)-L-α-aminoadipic acid α-benzhydryl ester

L-homoglutamic acid

(2S)-2-[(phenylmethoxy)carbonyl]aminoadipic acid

Refernces

• 1、 McCarthy, Blaine G.,Macarthur, Nicholas S.,Jakobsche, Charles E.. "A simple synthesis of 6-hydroxynorleucine based on the rearrangement of an N-nitrosodichloroacetamide". . p. 502 - 504. Retrieved 2016/01/12.
• 2、 -. "Nitrilases, nucleic acids encoding them and methods for making and using them". Page/Page column 52; 53. . Retrieved 2016/01/09.