ethyl (2E,5S,6S)-6-[(tert-butoxycarbonyl)amino]-5-(hydroxymethyl)-6-(4-methylphenyl)hex-2-enoate

Base Information

• Chemical Name: ethyl (2E,5S,6S)-6-[(tert-butoxycarbonyl)amino]-5-(hydroxymethyl)-6-(4-methylphenyl)hex-2-enoate
• CAS No.: 1202366-13-9
• Molecular Formula: C₂₁H₃₁NO₅
• Molecular Weight: 377.481
• Mol file: 1202366-13-9.mol

Synonyms:ethyl (2E,5S,6S)-6-[(tert-butoxycarbonyl)amino]-5-(hydroxymethyl)-6-(4-methylphenyl)hex-2-enoate

Chemical Property of ethyl (2E,5S,6S)-6-[(tert-butoxycarbonyl)amino]-5-(hydroxymethyl)-6-(4-methylphenyl)hex-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2E,5S,6S)-6-[(tert-butoxycarbonyl)amino]-5-(hydroxymethyl)-6-(4-methylphenyl)hex-2-enoate

There total 1 articles about ethyl (2E,5S,6S)-6-[(tert-butoxycarbonyl)amino]-5-(hydroxymethyl)-6-(4-methylphenyl)hex-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 (2E)-6-oxohex-2-enoate (71778-56-8) + 4-methylbenzaldehyde N-(tert-butoxycarbonyl)imine (479423-39-7) → ethyl (2E,5S,6S)-6-[(tert-butoxycarbonyl)amino]-5-(hydroxymethyl)-6-(4-methylphenyl)hex-2-enoate (1202366-13-9)

Guidance literature:

ethyl (2E)-6-oxohex-2-enoate; 4-methylbenzaldehyde N-(tert-butoxycarbonyl)imine; With L-proline; In acetonitrile; at 0 ℃; Inert atmosphere;

With sodium tetrahydroborate; acetic acid; In ethyl acetate; acetonitrile; for 0.0833333h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.200900787

Reference yield: 100.0%

ethyl (2E,5S,6S)-6-[(tert-butoxycarbonyl)amino]-5-(hydroxymethyl)-6-(4-methylphenyl)hex-2-enoate (1202366-13-9) + tert-butyldimethylsilyl chloride (18162-48-6) → ethyl (2E,5S,6S)-6-[(tert-butoxycarbonyl)amino]-5-{[(tert-butyldimethylsilyl)oxy]methyl}-6-(4-methylphenyl)hex-2-enoate (1202366-21-9)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.200900787

upstream raw materials:

ethyl (2E)-6-oxohex-2-enoate

4-methylbenzaldehyde N-(tert-butoxycarbonyl)imine

Downstream raw materials:

ethyl (2E,5S,6S)-6-[(tert-butoxycarbonyl)amino]-5-{[(tert-butyldimethylsilyl)oxy]methyl}-6-(4-methylphenyl)hex-2-enoate