dimethyl 1-benzyloxycarbonylamino-2-phenylethyl phosphonate

Base Information

• Chemical Name: dimethyl 1-benzyloxycarbonylamino-2-phenylethyl phosphonate
• CAS No.: 84690-42-6
• Molecular Formula: C₁₈H₂₂NO₅P
• Molecular Weight: 363.35
• Mol file: 84690-42-6.mol

Synonyms:dimethyl 1-benzyloxycarbonylamino-2-phenylethyl phosphonate

Chemical Property of dimethyl 1-benzyloxycarbonylamino-2-phenylethyl phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl 1-benzyloxycarbonylamino-2-phenylethyl phosphonate

There total 8 articles about dimethyl 1-benzyloxycarbonylamino-2-phenylethyl phosphonate 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: 82.0%

[1-(N-benzyloxycarbonylamino)-2-phenylethyl]triphenylphosphonium tetrafluoroborate + phosphorous acid trimethyl ester (121-45-9) → dimethyl 1-benzyloxycarbonylamino-2-phenylethyl phosphonate (84690-42-6)

Guidance literature:

With methyl-triphenylphosphonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 60 ℃; for 2h; Sealed tube;

DOI:10.1080/10426507.2012.744014

Reference yield:

[1-(N-benzyloxycarbonylamino)-2-phenylethyl]triphenylphosphonium tetrafluoroborate + Dimethyl phosphite (868-85-9) → dimethyl 1-benzyloxycarbonylamino-2-phenylethyl phosphonate (84690-42-6)

Guidance literature:

[1-(N-benzyloxycarbonylamino)-2-phenylethyl]triphenylphosphonium tetrafluoroborate; With tetrabutylammomium bromide; In toluene; for 0.166667h; Sonication;

Dimethyl phosphite; With potassium hydroxide; In toluene; at -70 ℃; for 72h; enantioselective reaction;

DOI:10.3390/molecules25020405

Reference yield:

dimethyl (E)-α-((benzyloxycarbonyl)amino)-β-phenylethenephosphonate → dimethyl 1-benzyloxycarbonylamino-2-phenylethyl phosphonate (84690-42-6)

Guidance literature:

With hydrogen; [(1,1-bis((i-Pr)2-phosphino)ferrocenyl)Rh(COD)]OTf; In methanol; at 25 ℃; under 3040.2 Torr;

DOI:10.1021/ol9906099

upstream raw materials:

methanol

diphenyl α-N-(benzyloxycarbonyl)amino-2-phenylethylphosphonate

Z-DL-Phe-OH

phosphorous acid trimethyl ester

Downstream raw materials:

methyl (2S)-2-<amino>ethyl>phosphinyl>oxy>-4-methylpentanoate

(S)-2-[(1-Benzyloxycarbonylamino-2-phenyl-ethyl)-hydroxy-phosphinoyloxy]-4-methyl-pentanoic acid

(2S)-2-<oxy>-4-methylpentanoate

(1-amino-2-phenylethyl)phosphonic acid, dimethyl ester

Refernces

• 1、 Ku?nik, Anna,Pa?dzierniok-Holewa, Agnieszka,Stecko, Sebastian,Wal?cka-Kurczyk, Alicja,Walczak, Krzysztof. "The Synthesis of α-Aminophosphonates via Enantioselective Organocatalytic Reaction of 1-(N-Acylamino)alkylphosphonium Salts with Dimethyl Phosphite". . . Retrieved 2020/01/28.
• 2、 Burk, Mark J.,Stammers, Timothy A.,Straub, Judith A.. "Enantioselective synthesis of α-hydroxy and α-amino phosphonates via catalytic asymmetric hydrogenation". . p. 387 - 390. Retrieved 2008/02/11.