1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester

Base Information

• Chemical Name: 1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester
• CAS No.: 82629-22-9
• Molecular Formula: C₁₂H₁₈NO₅P
• Molecular Weight: 287.252
• Mol file: 82629-22-9.mol

Synonyms:1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester

Chemical Property of 1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester

There total 10 articles about 1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl 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: 89.0%

methanol (67-56-1) + diphenyl 1-(phenylmethoxycarbonylamino)ethyl phosphonate (65164-80-9) → 1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester (82629-22-9)

Guidance literature:

With potassium fluoride; 18-crown-6 ether; 1.) reflux, 10 min 2.) room temp., overnight;

DOI:10.1055/s-1982-29817

Reference yield: 88.0%

diphenyl 1-(phenylmethoxycarbonylamino)ethyl phosphonate (65164-80-9) + sodium methylate (124-41-4) → 1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester (82629-22-9)

Guidance literature:

With methanol; In 1,4-dioxane; methanol; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2011.10.094

Reference yield: 78.0%

N-benzyloxycarbonylalanine (4132-86-9,26607-51-2,1142-20-7) + phosphorous acid trimethyl ester (121-45-9) → 1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester (82629-22-9)

Guidance literature:

N-benzyloxycarbonylalanine; With methanol; at 10 ℃; Electrolysis;

With triphenylphosphonium tetrafluoroborate; In dichloromethane; at 20 ℃; for 0.5h;

phosphorous acid trimethyl ester; With methyl-triphenylphosphonium iodide; N-ethyl-N,N-diisopropylamine; at 60 ℃; for 2h;

DOI:10.1016/j.molcatb.2016.05.011

upstream raw materials:

methanol

diphenyl 1-(phenylmethoxycarbonylamino)ethyl phosphonate

O-benzyl carbamate

sodium methylate

Downstream raw materials:

N-benzyloxycarbonyl-1-aminoethanephosphonic acid methyl monoester

N-[(1-benzyloxycarbonylamino-2-methyl)methoxyphosphinyl]glycine

N-[(1-benzyloxycarbonylamino-2-methyl)methoxyphosphinyl]alanine

N-[(1-benzyloxycarbonylamino-2-methyl)methoxyphosphinyl]valine

Refernces

• 1、 Zielińska, Katarzyna,Mazurkiewicz, Roman,Szymańska, Katarzyna,Jarz?bski, Andrzej,Magiera, Sylwia,Erfurt, Karol. "Penicillin G acylase-mediated kinetic resolution of racemic 1-(N-acylamino)alkylphosphonic and 1-(N-acylamino)alkylphosphinic acids and their esters". . p. 31 - 40. Retrieved 2016/07/19.
• 2、 Jia, Chao,Yang, Ke-Wu,Liu, Cheng-Cheng,Feng, Lei,Xiao, Jian-Min,Zhou, Li-Sheng,Zhang, Yi-Lin. "Synthesis, characterization and activity of new phosphonate dipeptides as potential inhibitors of VanX". . p. 482 - 484. Retrieved 2012/03/11.