(2S,3S)-2-(benzylamino)-3-methylpentanoic acid

Base Information

• Chemical Name: (2S,3S)-2-(benzylamino)-3-methylpentanoic acid
• CAS No.: 1859-49-0
• Molecular Formula: C13H19 N O2
• Molecular Weight: 221.299
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID40426402
• Nikkaji Number: J309.018C
• Mol file: 1859-49-0.mol

Synonyms:1859-49-0;BZL-ILE-OH;Benzyl-L-isoleucine;n-benzyl-l-isoleucine;(2S,3S)-2-(benzylamino)-3-methylpentanoic acid;N-benzyl-isoleucine;(2S,3S)-2-(benzylazaniumyl)-3-methylpentanoate;benzylisoleucine;L-Isoleucine, N-(phenylmethyl)-;SCHEMBL5658130;L-Isoleucine,N-(phenylmethyl)-;DTXSID40426402;GPAVORZIWQTJJQ-JQWIXIFHSA-N;CS-M2901;MFCD00038331;AKOS026357474;FD21821;AS-49211;HY-78906;Z1860298888

Chemical Property of (2S,3S)-2-(benzylamino)-3-methylpentanoic acid

Chemical Property:

• PSA: 49.33000
• LogP: 2.66640
• Storage Temp.: Store at RT.
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 221.141578849
• Heavy Atom Count: 16
• Complexity: 212

Purity/Quality:

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

Benzyl-L-isoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)NCC1=CC=CC=C1
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)O)NCC1=CC=CC=C1
• Uses: Bzl-Ile-OH is a reagent used for synthesizing hydrazinopeptides. It can also be converted into amino-derivatives with ammonium formate as a catalytic hydrogen transfer agent.

Technology Process of (2S,3S)-2-(benzylamino)-3-methylpentanoic acid

There total 7 articles about (2S,3S)-2-(benzylamino)-3-methylpentanoic 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%

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) → Bzl-Ile-OH (1859-49-0)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 0.133333h; Heating;

DOI:10.1016/S0040-4039(00)95769-1

Reference yield: 93.2%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + benzaldehyde (100-52-7) → (2S,3S)-2-(benzylamino)-3-methylpentanoic acid (1859-49-0)

Guidance literature:

L-isoleucine; benzaldehyde; With sodium hydroxide; In water; at 20 ℃; for 0.5h;

With sodium tetrahydroborate; In water; at 5 - 20 ℃; for 3.5h;

Reference yield: 55.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + benzyl bromide (100-39-0) → (2S,3S)-2-(benzylamino)-3-methylpentanoic acid (1859-49-0)

Guidance literature:

With caesium carbonate; In water; N,N-dimethyl-formamide; at 23 ℃; for 3.5h;

DOI:10.1021/jo010643c

upstream raw materials:

L-isoleucine

benzaldehyde

benzyl bromide

C₁₃H₁₇NO₂

Downstream raw materials:

N-Acetoacetyl-N-benzyl-isoleucin

(2S,3S)-2-(benzyl(methyl)amino)-3-methylpentanoic acid

(2S,3 S)-2-[benzyl(methyl)amino]-3-methylpentan-1-ol

(2S,3S)-2-(benzyl(methyl)amino)-3-methylpentanal

Refernces

• 1、 -. "CONJUGATE OF MONOMETHYL AURISTATIN F AND TRASTUZUMAB AND ITS USE FOR THE TREATMENT OF CANCER". Page/Page column 39. . Retrieved 2016/11/17.
• 2、 -. "ANTIBODY-DRUG-CONJUGATE AND ITS USE FOR THE TREATMENT OF CANCER". Page/Page column 129. . Retrieved 2015/11/10.