(2S,3R)-2-azaniumyl-3-methylpentanoate

Base Information

• Chemical Name: (2S,3R)-2-azaniumyl-3-methylpentanoate
• CAS No.: 3107-04-8
• Molecular Formula: C6H13NO2
• Molecular Weight: 131.175
• Hs Code.: 2922499990
• Mol file: 3107-04-8.mol

Synonyms:(2S,3R)-2-azaniumyl-3-methylpentanoate;alle;L-alloisoleucine zwitterion;CHEBI:85338;(+)-threo-2-amino-3-methylpentanoate

Chemical Property of (2S,3R)-2-azaniumyl-3-methylpentanoate

Chemical Property:

• Melting Point: ~285 °C (dec.)
• Boiling Point: 225.772 °C at 760 mmHg
• Flash Point: 90.344 °C
• PSA: 63.32000
• Density: 1.036 g/cm³
• LogP: 1.14470
• Storage Temp.: Store at RT.
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 131.094628657
• Heavy Atom Count: 9
• Complexity: 97.7

Purity/Quality:

98%,99%, ^*data from raw suppliers

DL-allo-Isoleucine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)C(C(=O)[O-])[NH3+]
• Isomeric SMILES: CC[C@@H](C)[C@@H](C(=O)[O-])[NH3+]
• Uses: DL-allo-Isoleucine is used in the preparation of chiral pyrrolidone derivatives and their application as herbicides.

Technology Process of (2S,3R)-2-azaniumyl-3-methylpentanoate

There total 77 articles about (2S,3R)-2-azaniumyl-3-methylpentanoate 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: 83.0%

2-Azido-3-methyl-pentanoic acid (116847-34-8) → isoleucine (319-78-8,443-79-8,1509-34-8,1509-35-9,3107-04-8,7004-09-3,73-32-5,959215-79-3,18875-42-8)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(00)77143-7

Reference yield: 48.0%

DL-α-keto-β-methyl-n-valerate → isoleucine (319-78-8,443-79-8,1509-34-8,1509-35-9,3107-04-8,7004-09-3,73-32-5,959215-79-3,18875-42-8) + L-isoleucine (73-32-5,959215-79-3,18875-42-8)

Guidance literature:

With ammonium formate; tris hydrochloride; nicotinamide adenine dinucleotide; formate dehydrogenase; phenylalanine dehydrogenase; In water; at 30 ℃; for 24h;

Reference yield:

DL-isoleucyl-leucyl anhydride (91741-17-2) + sulfuric acid (7664-93-9) → isoleucine (319-78-8,443-79-8,1509-34-8,1509-35-9,3107-04-8,7004-09-3,73-32-5,959215-79-3,18875-42-8) + LEUCINE (328-39-2,21675-61-6,25248-98-0,70-45-1)

Guidance literature:

Hydrolysis;

upstream raw materials:

D-Isoleucine

D,L-β-methylenenorvaline

2-Azido-3-methyl-pentanoic acid

2-oxo-3(RS)-methylvaleric acid

Downstream raw materials:

N-formyl-DL-alloisoleucine

N-formyl-isoleucine

2-Methylbutyraldehyde

L-isoleucine

Refernces

• 1、 Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko. "Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols". supporting information. p. 709 - 713. Retrieved 2019/01/25.
• 2、 Park, Eul-Soo,Dong, Joo-Young,Shin, Jong-Shik. "Biocatalytic asymmetric synthesis of unnatural amino acids through the cascade transfer of amino groups from primary amines onto keto acids". . p. 3538 - 3542. Retrieved 2014/01/06.