(S)-4-(benzylamino)-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-pentenoic acid ethyl ester

Base Information

• Chemical Name: (S)-4-(benzylamino)-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-pentenoic acid ethyl ester
• CAS No.: 131110-81-1
• Molecular Formula: C₂₀H₃₃NO₃Si
• Molecular Weight: 363.572
• Mol file: 131110-81-1.mol

Synonyms:(S)-4-(benzylamino)-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-pentenoic acid ethyl ester

Chemical Property of (S)-4-(benzylamino)-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-pentenoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(benzylamino)-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-pentenoic acid ethyl ester

There total 17 articles about (S)-4-(benzylamino)-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-pentenoic acid ethyl ester 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: 70.0%

(S)-4-(benzylamino)-5-hydroxy-2-pentenoic acid ethyl ester (134930-26-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (S)-4-(benzylamino)-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-pentenoic acid ethyl ester (131110-81-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 4h;

DOI:10.1021/jo00049a040

Reference yield:

(S)-3-benzyl-2,2-dimethyl-4-oxazolidinemethanol (131110-78-6) → (S)-4-(benzylamino)-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-pentenoic acid ethyl ester (131110-81-1)

Guidance literature:

Multi-step reaction with 3 steps

2: aq. HCl / ethanol / 18 h / Ambient temperature

3: 70 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h

With hydrogenchloride; dmap; triethylamine; In ethanol; dichloromethane;

DOI:10.1021/jo00049a040

Reference yield:

methyl (2R)-2-(benzylamino)-3-hydroxypropanoate (123639-56-5,131110-76-4,144001-42-3) → (S)-4-(benzylamino)-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-pentenoic acid ethyl ester (131110-81-1)

Guidance literature:

Multi-step reaction with 5 steps

1: p-TSA, molecular sieves 4 Angstroem / benzene / 24 h / Heating

2: LiAlH₄ / diethyl ether / 1 h / below 3 deg C

4: aq. HCl / ethanol / 18 h / Ambient temperature

5: 70 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h

With hydrogenchloride; dmap; lithium aluminium tetrahydride; 4 A molecular sieve; toluene-4-sulfonic acid; triethylamine; In diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1021/jo00049a040

upstream raw materials:

(S)-4-(benzylamino)-5-hydroxy-2-pentenoic acid ethyl ester

tert-butyldimethylsilyl chloride

(S)-3-benzyl-2,2-dimethyl-4-oxazolidinemethanol

(R)-3-Hydroxy-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester

Downstream raw materials:

(E)-(S)-4-[Benzyl-(2,2,2-trichloro-acetyl)-amino]-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enoic acid ethyl ester

<2S-(2α,3β,4α)>-4-acetyl-1-benzyl-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-3-pyrrolidineacetic acid ethyl ester

(1α,3aα,7aα)-octahydro-2-benzyl-1-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-6-oxopyrano<3,4-c>pyrrole

(2α,3β,4α)-1-benzyl-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-(hydroxymethyl)-3-pyrrolidineacetic acid ethyl ester