N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester

Base Information

• Chemical Name: N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester
• CAS No.: 1384458-03-0
• Molecular Formula: C₂₇H₄₄N₃O₉P
• Molecular Weight: 585.635
• Mol file: 1384458-03-0.mol

Synonyms:N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester

Chemical Property of N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester

There total 4 articles about N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester 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: 61.0%

N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-L-threonine methyl ester (1402348-91-7) + triethyl phosphite (122-52-1) → N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester (1384458-03-0)

Guidance literature:

N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-L-threonine methyl ester; With iodine; lead(IV) tetraacetate; In dichloromethane; at 26 ℃; for 1h; Inert atmosphere; Irradiation;

triethyl phosphite; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol301676z

Reference yield:

N-benzyloxycarbonyl-L-leucyl-L-leucine (7801-71-0) → N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester (1384458-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 26 °C / Inert atmosphere

2.1: iodine; lead(IV) tetraacetate / dichloromethane / 1 h / 26 °C / Inert atmosphere; Irradiation

2.2: 3 h / 0 °C / Inert atmosphere

With iodine; lead(IV) tetraacetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ol301676z

Reference yield:

C25H37N3O8 + triethyl phosphite (122-52-1) → N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester (1384458-03-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1002/chem.201703758

upstream raw materials:

N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-L-threonine methyl ester

triethyl phosphite

N-benzyloxycarbonyl-L-leucyl-L-leucine

Downstream raw materials:

(Z)-N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-α,β-dehydro-5-(phenyl)norvaline methyl ester

Refernces

• 1、 Saavedra, Carlos J.,Boto, Alicia,Hernandez, Rosendo. " Customizable units in Di- and tripeptides: Selective conversion into substituted dehydroamino acids". supporting information; experimental part. p. 3788 - 3791. Retrieved 2012/09/08.