(4S,1'RS)-1,1-Dimethylethyl 4-<3'-methoxy-3'-oxo-1'-benzylpropyl>-2,2-dimethyl-3-oxazolidinecarboxylate

Base Information

• Chemical Name: (4S,1'RS)-1,1-Dimethylethyl 4-<3'-methoxy-3'-oxo-1'-benzylpropyl>-2,2-dimethyl-3-oxazolidinecarboxylate
• CAS No.: 129483-74-5
• Molecular Formula: C₂₁H₃₁NO₅
• Molecular Weight: 377.481
• Mol file: 129483-74-5.mol

Synonyms:

Chemical Property of (4S,1'RS)-1,1-Dimethylethyl 4-<3'-methoxy-3'-oxo-1'-benzylpropyl>-2,2-dimethyl-3-oxazolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,1'RS)-1,1-Dimethylethyl 4-<3'-methoxy-3'-oxo-1'-benzylpropyl>-2,2-dimethyl-3-oxazolidinecarboxylate

There total 8 articles about (4S,1'RS)-1,1-Dimethylethyl 4-<3'-methoxy-3'-oxo-1'-benzylpropyl>-2,2-dimethyl-3-oxazolidinecarboxylate 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: 86.0%

(4S)-1,1-Dimethylethyl 4-(3'-methoxy-3'-oxo-1'-propenyl)-2,2-dimethyl-3-oxazolidinecarboxylate (353520-76-0) → (4S,1'RS)-1,1-Dimethylethyl 4-<3'-methoxy-3'-oxo-1'-benzylpropyl>-2,2-dimethyl-3-oxazolidinecarboxylate (129483-74-5,129483-79-0)

Guidance literature:

With chloro-trimethyl-silane; In tetrahydrofuran; diethyl ether; 1.) -40 deg C, 1 h, 2.) -40 deg C to r.t. over 3 h;

DOI:10.1021/jo00019a055

Reference yield:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → (4S,1'RS)-1,1-Dimethylethyl 4-<3'-methoxy-3'-oxo-1'-benzylpropyl>-2,2-dimethyl-3-oxazolidinecarboxylate (129483-74-5,129483-79-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / tetra-n-butylammonium iodide, 3 M aq. K₂CO₃ / 16 h / Ambient temperature

2: 86 percent / TMSCl / tetrahydrofuran; diethyl ether / 1.) -40 deg C, 1 h, 2.) -40 deg C to r.t. over 3 h

With chloro-trimethyl-silane; tetra-(n-butyl)ammonium iodide; potassium carbonate; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00019a055

Reference yield:

4-Formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (95715-87-0,102308-32-7,127589-93-9,144070-30-4) → 4-(1-Methoxycarbonylmethyl-2-phenyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (129483-74-5,129483-79-0)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃

2: 1) CuBr-Me₂S, LiBr 2) Me₃SiCl / 2) Et₂O, -45 deg C

With chloro-trimethyl-silane; potassium carbonate; lithium bromide;

DOI:10.1016/S0040-4039(00)94416-2

upstream raw materials:

phenylmagnesium bromide

4-Formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

4-Formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S)-1,1-Dimethylethyl 4-(3'-methoxy-3'-oxo-1'-propenyl)-2,2-dimethyl-3-oxazolidinecarboxylate

Downstream raw materials:

(4R,5S)-5<<(1,1-Dimethylethoxy)carbonyl>amino>-4-benzyltetrahydro-2H-pyran-2-one

Methyl (3R,4S)-3-benzyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hydroxypentanoate

Dimethyl (2S,3R)-3-benzyl-2-<<(1,1-dimethylethoxy)carbonyl>amino>-1,5-pentanedioate

(2S,3R)-2-Amino-3-benzyl-1,5-pentanedioic acid hydrochloride

Refernces

• 1、 Jako,Uiber,Mann,Taddei,Wermuth. "Diastereoselectivity in conjugate addition of alkylcuprates to vinylogous ester of N,O-diprotected serinal". . p. 1011 - 1014. Retrieved 2007/10/02.