allyl 2-(N-tert-butoxycarbonyl)amino-4-[O-[N-(2-chlorobenzyloxycarbonyl)-N-methyl]amino]hydroxybutanoate

Base Information

• Chemical Name: allyl 2-(N-tert-butoxycarbonyl)amino-4-[O-[N-(2-chlorobenzyloxycarbonyl)-N-methyl]amino]hydroxybutanoate
• CAS No.: 475150-37-9
• Molecular Formula: C₂₁H₂₉ClN₂O₇
• Molecular Weight: 456.923
• Mol file: 475150-37-9.mol

Synonyms:allyl 2-(N-tert-butoxycarbonyl)amino-4-[O-[N-(2-chlorobenzyloxycarbonyl)-N-methyl]amino]hydroxybutanoate

Chemical Property of allyl 2-(N-tert-butoxycarbonyl)amino-4-[O-[N-(2-chlorobenzyloxycarbonyl)-N-methyl]amino]hydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-(N-tert-butoxycarbonyl)amino-4-[O-[N-(2-chlorobenzyloxycarbonyl)-N-methyl]amino]hydroxybutanoate

There total 6 articles about allyl 2-(N-tert-butoxycarbonyl)amino-4-[O-[N-(2-chlorobenzyloxycarbonyl)-N-methyl]amino]hydroxybutanoate 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-methyl-N-(2-chlorobenzyloxycarbonyl)hydroxylamine (271795-03-0) + allyl 2-(N-tert-butoxycarbonyl)amino-4-bromobutanoate (475150-36-8) → allyl 2-(N-tert-butoxycarbonyl)amino-4-[O-[N-(2-chlorobenzyloxycarbonyl)-N-methyl]amino]hydroxybutanoate (475150-37-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(02)01212-1

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → allyl 2-(N-tert-butoxycarbonyl)amino-4-[O-[N-(2-chlorobenzyloxycarbonyl)-N-methyl]amino]hydroxybutanoate (475150-37-9)

Guidance literature:

Multi-step reaction with 5 steps

1: NaOH / H₂O; acetonitrile / 14 h

2: 1.40 g / dimethylformamide / 19 h

3: Et₃N / CH₂Cl₂ / 1.58 h

4: 2.34 g / LiBr / CH₂Cl₂; acetone / 14 h

5: 93 percent / NaH / dimethylformamide / 1.5 h / 0 °C

With sodium hydroxide; sodium hydride; triethylamine; lithium bromide; In dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo034984x

Reference yield:

L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid (41088-86-2) → allyl 2-(N-tert-butoxycarbonyl)amino-4-[O-[N-(2-chlorobenzyloxycarbonyl)-N-methyl]amino]hydroxybutanoate (475150-37-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.40 g / dimethylformamide / 19 h

2: Et₃N / CH₂Cl₂ / 1.58 h

3: 2.34 g / LiBr / CH₂Cl₂; acetone / 14 h

4: 93 percent / NaH / dimethylformamide / 1.5 h / 0 °C

With sodium hydride; triethylamine; lithium bromide; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo034984x

upstream raw materials:

N-methyl-N-(2-chlorobenzyloxycarbonyl)hydroxylamine

allyl 2-(N-tert-butoxycarbonyl)amino-4-bromobutanoate

di-tert-butyl dicarbonate

L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid

Downstream raw materials:

2-(N-tert-butoxycarbonyl)amino-4-[O-[N-(2-chlorobenzyloxycarbonyl)-N-methyl]amino]hydroxybutanoic acid

Refernces

• 1、 Carrasco, Michael R.,Brown, Ryan T.. "A Versatile Set of Aminooxy Amino Acids for the Synthesis of Neoglycopeptides". . p. 8853 - 8858. Retrieved 2007/10/03.