ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

Base Information

• Chemical Name: ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate
• CAS No.: 172900-76-4
• Molecular Formula: C₂₆H₄₃NO₇
• Molecular Weight: 481.63
• Mol file: 172900-76-4.mol

Synonyms:ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

Chemical Property of ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

There total 13 articles about ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate 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%

di-tert-butyl dicarbonate (24424-99-5) + (2S,4S)-2-Amino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-5-methyl-hexanoic acid ethyl ester (172900-99-1) → ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate (172900-76-4)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1002/hlca.200390235

Reference yield:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate (172900-76-4)

Guidance literature:

Multi-step reaction with 9 steps

1: NaBH₄ / ethanol

2: PBr₃ / CH₂Cl₂

3: 76 percent / LiHMDS / tetrahydrofuran

4: 81 percent / LiOH; H₂O₂

5: 95 percent / LAH / tetrahydrofuran

6: 97 percent / PPh₃; NBS / CH₂Cl₂

7: 68 percent / n-BuLi

8: HCl / acetonitrile

9: Et₃N

With hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; dihydrogen peroxide; phosphorus tribromide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2005.07.028

Reference yield:

(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid (172900-71-9) → ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate (172900-76-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / LAH / tetrahydrofuran

2: 97 percent / PPh₃; NBS / CH₂Cl₂

3: 68 percent / n-BuLi

4: HCl / acetonitrile

5: Et₃N

With hydrogenchloride; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2005.07.028

upstream raw materials:

di-tert-butyl dicarbonate

(2S,4S)-2-Amino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-5-methyl-hexanoic acid ethyl ester

(2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine

isovanillin

Downstream raw materials:

(2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexan-1-ol

(2S,4S)-2-tert-butoxycarbonylamino-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoic acid

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

[(1S,3S)-3-[4-Methoxy-3-(3-methoxy-propoxy)-benzyl]-1-(methoxy-methyl-carbamoyl)-4-methyl-pentyl]-carbamic acid tert-butyl ester