ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate

Base Information

• Chemical Name: ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate
• CAS No.: 852468-42-9
• Molecular Formula: C₂₇H₃₅NO₅
• Molecular Weight: 453.579
• Mol file: 852468-42-9.mol

Synonyms:ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate

Chemical Property of ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate

There total 9 articles about ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate 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: 76.0%

ethyl 2-diethoxyphosphorylpropionate (3699-66-9) + (S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde (169905-23-1) → ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate (852468-42-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 ℃; for 2h;

DOI:10.1016/j.tetlet.2005.02.166

Reference yield: 14.0%

ethyl 2-diethoxyphosphorylpropionate (3699-66-9) + (S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde (169905-23-1) → ethyl (4S,2Z)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate (852468-43-0) + ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate (852468-42-9) + ethyl (4R,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate

Guidance literature:

ethyl 2-diethoxyphosphorylpropionate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.666667h;

(S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1021/jo0625608

Reference yield: 13.0%

(S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde (169905-23-1) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (4S,2Z)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate (852468-43-0) + ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate (852468-42-9) + ethyl (4R,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate

Guidance literature:

In dichloromethane; at 0 - 20 ℃; Title compound not separated from byproducts;

DOI:10.1021/jo0625608

upstream raw materials:

ethyl 2-diethoxyphosphorylpropionate

(S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde

ethyl (triphenylphosphoranylidene)acetate

(2S)-methyl 2--3-phenyl-1-propanoate

Downstream raw materials:

4-benzyl-3-(4-methoxy-benzyl)-6-methyl-2-oxo-3-aza-tricyclo[5.2.2.0^1,5]undec-8-ene-6-carboxylic acid ethyl ester

(2R)-2-[(3S,4S)-3-benzyl-2-(4-methoxybenzyl)-1-oxo-2-azaspiro[4.5]decan-4-yl]propanol

ethyl (2R)-2-[(3S,4S)-3-benzyl-2-(4-methoxybenzyl)-1-oxo-2-azaspiro[4.5]decan-4-yl]propanoate

ethyl (4S,2E)-4-(4-methoxybenzylamino)-2-methyl-5-phenylpent-2-enoate