benzyl (2S)-2-(benzyloxycarbonylamino)-6-[2-(4-imidazolyl)ethyl](piperonyl)amino-4-hexenoate

Base Information

• Chemical Name: benzyl (2S)-2-(benzyloxycarbonylamino)-6-[2-(4-imidazolyl)ethyl](piperonyl)amino-4-hexenoate
• CAS No.: 876062-23-6
• Molecular Formula: C₃₄H₃₆N₄O₆
• Molecular Weight: 596.683
• Mol file: 876062-23-6.mol

Synonyms:benzyl (2S)-2-(benzyloxycarbonylamino)-6-[2-(4-imidazolyl)ethyl](piperonyl)amino-4-hexenoate

Chemical Property of benzyl (2S)-2-(benzyloxycarbonylamino)-6-[2-(4-imidazolyl)ethyl](piperonyl)amino-4-hexenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S)-2-(benzyloxycarbonylamino)-6-[2-(4-imidazolyl)ethyl](piperonyl)amino-4-hexenoate

There total 6 articles about benzyl (2S)-2-(benzyloxycarbonylamino)-6-[2-(4-imidazolyl)ethyl](piperonyl)amino-4-hexenoate 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: 71.0%

Nα-piperonylhistamine (857795-24-5) + benzyl (2S)-4-acetoxy-2-(benzyloxycarbonylamino)-5-hexenoate (876062-19-0) → benzyl (2S)-2-(benzyloxycarbonylamino)-6-[2-(4-imidazolyl)ethyl](piperonyl)amino-4-hexenoate (876062-23-6)

Guidance literature:

With triphenylphosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; at 50 ℃; for 2h;

DOI:10.1055/s-2005-918447

Reference yield:

piperonal (120-57-0,30024-74-9) → benzyl (2S)-2-(benzyloxycarbonylamino)-6-[2-(4-imidazolyl)ethyl](piperonyl)amino-4-hexenoate (876062-23-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe; molecular sieves 3 Angstroem / methanol / 50 °C

2: 238 mg / NaBH₄ / methanol / -78 - 20 °C

3: 71 percent / PPh₃ / Pd₂(dba)3 / tetrahydrofuran / 1 h / 50 °C

With sodium tetrahydroborate; 3 A molecular sieve; sodium methylate; triphenylphosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol;

DOI:10.1016/j.tet.2006.07.080

Reference yield:

(R)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-iodopropanoate (65926-39-8) → benzyl (2S)-2-(benzyloxycarbonylamino)-6-[2-(4-imidazolyl)ethyl](piperonyl)amino-4-hexenoate (876062-23-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: zinc; TMSCl; 1,2-dibromoethane / dimethylformamide / 0.33 h / 60 °C

1.2: 98 percent / CuCN; LiCl / dimethylformamide / 2 h

2.1: 71 percent / PPh₃ / Pd₂(dba)3 / tetrahydrofuran / 1 h / 50 °C

With chloro-trimethyl-silane; ethylene dibromide; triphenylphosphine; zinc; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.07.080

upstream raw materials:

N^α-piperonylhistamine

benzyl (2S)-4-acetoxy-2-(benzyloxycarbonylamino)-5-hexenoate

benzo[1,3]dioxol-5-ylmethylene-[2-(3H-imidazol-4-yl)-ethyl]-amine

piperonal

Downstream raw materials:

(S)-gizzerosine