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

Base Information

• Chemical Name: <2S-(2α,3β,4α)>-4-acetyl-1-benzyl-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-3-pyrrolidineacetic acid ethyl ester
• CAS No.: 131110-82-2
• Molecular Formula: C₂₄H₃₉NO₄Si
• Molecular Weight: 433.663
• Mol file: 131110-82-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about <2S-(2α,3β,4α)>-4-acetyl-1-benzyl-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-3-pyrrolidineacetic 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: 90.0%

(S)-4-(benzylamino)-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-pentenoic acid ethyl ester (131110-81-1) + methyl vinyl ketone (78-94-4,25038-87-3) → <2S-(2α,3β,4α)>-4-acetyl-1-benzyl-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-3-pyrrolidineacetic acid ethyl ester (131110-82-2)

Guidance literature:

With 1,1,3,3-tetramethylguanidine; In ethanol;

DOI:10.1016/S0040-4039(00)97768-2

Reference yield:

(S)-3-benzyl-2,2-dimethyl-4-oxazolidinemethanol (131110-78-6) → <2S-(2α,3β,4α)>-4-acetyl-1-benzyl-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-3-pyrrolidineacetic acid ethyl ester (131110-82-2)

Guidance literature:

Multi-step reaction with 4 steps

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

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

4: 2) tetramethylguanidine (TMG) / 1) EtOH, r.t., 3 d, 2) 2h

With hydrogenchloride; dmap; 1,1,3,3-tetramethylguanidine; triethylamine; In ethanol; dichloromethane;

DOI:10.1021/jo00049a040

Reference yield:

(R)-3-benzyl-2,2-dimethyl-4-oxazolidinecarboxylic acid methyl ester (131110-77-5) → <2S-(2α,3β,4α)>-4-acetyl-1-benzyl-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-3-pyrrolidineacetic acid ethyl ester (131110-82-2)

Guidance literature:

Multi-step reaction with 5 steps

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

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

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

5: 2) tetramethylguanidine (TMG) / 1) EtOH, r.t., 3 d, 2) 2h

With hydrogenchloride; dmap; lithium aluminium tetrahydride; 1,1,3,3-tetramethylguanidine; triethylamine; In diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00049a040

upstream raw materials:

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

methyl vinyl ketone

(E)-(S)-4-[Benzyl-(3-oxo-butyl)-amino]-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enoic acid ethyl ester

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

Downstream raw materials:

(-)-kainic acid