(S)-Benzyl (1-cyano-3-methylbutyl)carbamate

Base Information

• Chemical Name: (S)-Benzyl (1-cyano-3-methylbutyl)carbamate
• CAS No.: 3589-42-2
• Molecular Formula: C14H18N2O2
• Molecular Weight: 246.309
• DSSTox Substance ID: DTXSID401221269
• Nikkaji Number: J2.479.583G
• Mol file: 3589-42-2.mol

Synonyms:3589-42-2;(S)-Benzyl (1-cyano-3-methylbutyl)carbamate;(S)-N-Cbz-Leucinenitrile;(S)-benzyl 1-cyano-3-methylbutylcarbamate;BENZYL N-[(1S)-1-CYANO-3-METHYLBUTYL]CARBAMATE;AC-7665;(S)-Benzyl(1-cyano-3-methylbutyl)carbamate;SCHEMBL7412569;DTXSID401221269;AKOS005146166;AKOS015840714;Phenylmethyl N-[(1S)-1-cyano-3-methylbutyl]carbamate

Chemical Property of (S)-Benzyl (1-cyano-3-methylbutyl)carbamate

Chemical Property:

• Boiling Point: 405.4 °C at 760 mmHg
• Flash Point: 199 °C
• PSA: 62.12000
• Density: 1.081 g/cm³
• LogP: 3.24198
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 246.136827821
• Heavy Atom Count: 18
• Complexity: 300

Purity/Quality:

99% ^*data from raw suppliers

(S)-Benzyl(1-cyano-3-methylbutyl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C#N)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)C[C@@H](C#N)NC(=O)OCC1=CC=CC=C1

Technology Process of (S)-Benzyl (1-cyano-3-methylbutyl)carbamate

There total 8 articles about (S)-Benzyl (1-cyano-3-methylbutyl)carbamate 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%

N-carbobenzoxy-L-leucinal (70853-26-8,86852-22-4,71413-15-5) → (S)-2-(benzyloxycarbonylamino)-4-methylpentanenitrile (3589-42-2)

Guidance literature:

With ammonium hydroxide; iodine; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/jo0625352

Reference yield:

N-benzyloxycarbonyl-L-leucinamide (4801-79-0) → (S)-2-(benzyloxycarbonylamino)-4-methylpentanenitrile (3589-42-2)

Guidance literature:

With pyridine; trichlorophosphate;

Reference yield:

methoxycarbonylsulfamoyl-triethylammmonium hydroxide → (S)-2-(benzyloxycarbonylamino)-4-methylpentanenitrile (3589-42-2)

Guidance literature:

In tetrahydrofuran;

upstream raw materials:

N-benzyloxycarbonyl-L-leucinamide

N-carbobenzoxy-L-leucinal

Z-Leu-OH

L-leucine

Downstream raw materials:

(S)-2-benzyloxycarbonylamino-4-methyl-pentanimidic acid ethyl ester

(S)-2-(N-benzyl-N-benzyloxycarbonylamino)-isohexanonitrile

(S)-1-benzyl-4-[(Z)-tert-butyloxycarbonylmethylidene]-5-(2-methylpropyl)-imidazolidin-2-one

(4S,5S)-4-(2-hydroxyethyl)-5-(2-methylpropyl)-1-phenylmethyl-imidazolidin-2-one

Refernces

• 1、 Cam, Thuy Hoang,Bouillere, Francelin,Johannesen, Sine,Zulauf, Anais,Panel, Cecilia,Pouilhes, Annie,Gori, Didier,Alezra, Valerie,Kouklovsky, Cyrille. "AmIno Acid Homologation by the Blaise Reaction: A new entry into nitrogen heterocycles". experimental part. p. 4177 - 4187. Retrieved 2009/09/08.
• 2、 Hoang, Cam Thuy,Alezra, Valerie,Guillot, Regis,Kouklovsky, Cyrille. "A Stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of α-aminoacids". . p. 2521 - 2524. Retrieved 2008/02/05.