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

Base Information

• Chemical Name: N-alpha-Benzyloxycarbonyl-L-valinyl-diazomethane, (3S)-3-Z-amino-1-diazo-4-methyl-2-pentanone
• CAS No.: 90105-46-7
• Molecular Formula: C14H17 N3 O3
• Molecular Weight: 275.307
• Mol file: 90105-46-7.mol

Synonyms:Carbamicacid, [(1S)-3-diazo-1-(1-methylethyl)-2-oxopropyl]-, phenylmethyl ester (9CI);Carbamic acid, [3-diazo-1-(1-methylethyl)-2-oxopropyl]-, phenylmethyl ester,(S)-

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

Chemical Property:

• PSA: 92.79000
• LogP: 2.27906

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 6 articles about N-alpha-Benzyloxycarbonyl-L-valinyl-diazomethane, (3S)-3-Z-amino-1-diazo-4-methyl-2-pentanone 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%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (S)-N-(benzyloxycarbonyl)valine (1149-26-4) → benzyl (S)-(1-diazo-4-methyl-2-oxopentan-3-yl)carbamate (90105-46-7,28094-73-7)

Guidance literature:

(S)-N-(benzyloxycarbonyl)valine; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; diethyl ether; at -25 ℃; for 0.5h;

diazomethane; In tetrahydrofuran; diethyl ether; at -10 - 20 ℃; for 3h;

DOI:10.1016/j.tetasy.2005.01.049

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + C16H21NO6 (119153-86-5) → benzyl (S)-(1-diazo-4-methyl-2-oxopentan-3-yl)carbamate (90105-46-7,28094-73-7)

Guidance literature:

In diethyl ether; at -10 ℃; for 3h;

DOI:10.3390/12051183

Reference yield:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) → benzyl (S)-(1-diazo-4-methyl-2-oxopentan-3-yl)carbamate (90105-46-7,28094-73-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / diethyl ether; tetrahydrofuran / 0.5 h / -25 °C

2: diethyl ether / 3 h / -10 °C

With triethylamine; In tetrahydrofuran; diethyl ether;

DOI:10.3390/12051183

upstream raw materials:

diazomethane

(S)-N-(benzyloxycarbonyl)valine

chloroformic acid ethyl ester

C₁₆H₂₁NO₆

Downstream raw materials:

Methyl (R)-(-)-N-benzyloxycarbonylamino-4-methylpentanoate

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

benzyl (3S)-1-(2-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-1-diazo-4-methyl-2-oxopentan-3-ylcarbamate

(R)-3-<(benzyoxycarbonyl)amino>-4-methylpentanoic acid