(2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester
CAS No.:860453-69-6
Molecular Formula:C₂₆H₄₁NO₆Si
Molecular Weight:491.7
Hs Code.:

(2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Synonyms:(2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

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Chemical Property of (2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

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Technology Process of (2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

There total 7 articles about (2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl 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: 85.0%

: 857311-65-0
(2R,3S)-2-Acetyl-2-[acryloyl-(4-methoxy-benzyl)-amino]-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid methyl ester

: 860453-69-6
(2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: (2R,3S)-2-Acetyl-2-[acryloyl-(4-methoxy-benzyl)-amino]-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid methyl ester; With titanium(IV) isopropylate; cyclopentylmagnesium chloride; In diethyl ether; at -40 ℃; for 0.5h;

With iodine; In tetrahydrofuran; diethyl ether; at -40 - 23 ℃; for 4h;

With triethylamine; In dichloromethane; for 0.5h;
DOI:10.1021/ja052376o

Reference yield:

: 860453-75-4
(4R,5R)-4-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

: 860453-69-6
(2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

2.1: NaCNBH₃; Et₃N; AcOH / 24 h / 40 °C

3.1: 5.0 g / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -78 °C

4.1: 79 percent / triisobutylamine / acetonitrile / 72 h / 23 °C

5.1: Ti(OiPr)4; c-C₅H₉MgCl / diethyl ether; various solvent(s) / 0.5 h / -40 °C

5.2: I₂ / tetrahydrofuran; diethyl ether; various solvent(s) / 4 h / -40 - 23 °C

5.3: 85 percent / Et₃N / CH₂Cl₂ / 0.5 h

With 2,6-dimethylpyridine; titanium(IV) isopropylate; oxalyl dichloride; triisobutylamine; cyclopentylmagnesium chloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; triethylamine; In diethyl ether; dichloromethane; acetonitrile; 3.1: Swern oxidation;
DOI:10.1021/ja052376o

Reference yield:

: 860453-67-4
(4S,5R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

: 860453-69-6
(2R,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaCNBH₃; Et₃N; AcOH / 24 h / 40 °C

2.1: 5.0 g / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -78 °C

3.1: 79 percent / triisobutylamine / acetonitrile / 72 h / 23 °C

4.1: Ti(OiPr)4; c-C₅H₉MgCl / diethyl ether; various solvent(s) / 0.5 h / -40 °C

4.2: I₂ / tetrahydrofuran; diethyl ether; various solvent(s) / 4 h / -40 - 23 °C

4.3: 85 percent / Et₃N / CH₂Cl₂ / 0.5 h

With titanium(IV) isopropylate; oxalyl dichloride; triisobutylamine; cyclopentylmagnesium chloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; triethylamine; In diethyl ether; dichloromethane; acetonitrile; 2.1: Swern oxidation;
DOI:10.1021/ja052376o