N-alpha-Benzyloxycarbonyl-L-isoleucinyl-diazomethane, (3S,4S)-3-Z-amino-1-diazo-4-methyl-2-hexanone

Base Information

• Chemical Name: N-alpha-Benzyloxycarbonyl-L-isoleucinyl-diazomethane, (3S,4S)-3-Z-amino-1-diazo-4-methyl-2-hexanone
• CAS No.: 114715-76-3
• Molecular Formula: C15H19 N3 O3
• Molecular Weight: 289.334
• Mol file: 114715-76-3.mol

Synonyms:Carbamicacid, [(1S,2S)-1-(diazoacetyl)-2-methylbutyl]-, phenylmethyl ester (9CI);Carbamic acid, [1-(diazoacetyl)-2-methylbutyl]-, phenylmethyl ester,[S-(R*,R*)]-

Chemical Property of N-alpha-Benzyloxycarbonyl-L-isoleucinyl-diazomethane, (3S,4S)-3-Z-amino-1-diazo-4-methyl-2-hexanone

Chemical Property:

• PSA: 92.79000
• LogP: 2.66916

Purity/Quality:

97% ^*data from raw suppliers

(3S,4S)-3-Z-AMINO-1-DIAZO-4-METHYL-2-HEXANONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-alpha-Benzyloxycarbonyl-L-isoleucinyl-diazomethane, (3S,4S)-3-Z-amino-1-diazo-4-methyl-2-hexanone

There total 3 articles about N-alpha-Benzyloxycarbonyl-L-isoleucinyl-diazomethane, (3S,4S)-3-Z-amino-1-diazo-4-methyl-2-hexanone 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: 89.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + N-Cbz-L-Isoleucine (3160-59-6) → (3-diazo-1-(S)-(1-methylpropyl)-2-oxopropyl)carbamic acid benzyl ester (114715-76-3,28094-25-9)

Guidance literature:

N-Cbz-L-Isoleucine; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; diethyl ether; at -25 ℃; for 0.5h;

diazomethane; In tetrahydrofuran; diethyl ether; at -10 - 100 ℃; for 3h;

DOI:10.1016/j.tetasy.2005.01.049

Reference yield:

N-Cbz-L-Isoleucine (3160-59-6) → (3-diazo-1-(S)-(1-methylpropyl)-2-oxopropyl)carbamic acid benzyl ester (114715-76-3,28094-25-9)

Guidance literature:

Multi-step reaction with 2 steps

2: diethyl ether

In diethyl ether; 1: Condensation / 2: Diazotization;

DOI:10.1039/a907948c

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + Z-Ile-O-COOiBu (41446-04-2) → (3-diazo-1-(S)-(1-methylpropyl)-2-oxopropyl)carbamic acid benzyl ester (114715-76-3,28094-25-9)

Guidance literature:

In diethyl ether;

DOI:10.1039/a907948c

upstream raw materials:

diazomethane

N-Cbz-L-Isoleucine

Z-Ile-O-COOiBu

Downstream raw materials:

(3-bromo-1-(S)-(1-methylpropyl)-2-oxopropyl)carbamic acid benzyl ester

[(1S,2S)-1-(2,2-Dihydroxy-acetyl)-2-methyl-butyl]-carbamic acid benzyl ester

[(1S,2S)-1-(2-Azido-acetyl)-2-methyl-butyl]-carbamic acid benzyl ester

2-phenyl-4-(1-(S)-benzyloxycarbonylamino-2-methylbutyl)-1H-imidazole