(2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester
• CAS No.: 267889-00-9
• Molecular Formula: C₃₃H₄₁NO₄SSi
• Molecular Weight: 575.844

Synonyms:(2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester

Chemical Property of (2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester

There total 13 articles about (2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-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: 90.0%

(2S,3R,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester (267888-99-3) → (2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester (267889-00-9)

Guidance literature:

With potassium carbonate; In methanol; for 0.5h;

DOI:10.1016/S0040-4039(00)00096-4

Reference yield:

2-[4-(benzyloxy)benzyl]acetic acid (6547-53-1) → (2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester (267889-00-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: DCC; HOBt

2.1: LAH

3.1: 82 percent / n-BuLi

4.1: 51 percent / LDA

5.1: H₂ / Pd/C

5.2: ethyl acetate / reflux

6.1: DMAP

7.1: P₄S₁₀; NaHCO₃

8.1: TsOH / methanol

9.1: Et₃N

10.1: 90 percent / K₂CO₃ / methanol / 0.5 h

With dmap; lithium aluminium tetrahydride; n-butyllithium; tetraphosphorus decasulfide; hydrogen; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; In methanol; 1.1: Acylation / 2.1: Reduction / 3.1: Addition / 4.1: Addition / 4.2: Addition / 5.1: Hydrogenolysis / 5.2: Cyclization / 6.1: silylation / 7.1: sulfuration / 8.1: desilylation / 9.1: silylation / 10.1: Isomerization;

DOI:10.1016/S0040-4039(00)00096-4

Reference yield:

(4-hydroxy-phenyl)-acetic acid ethyl ester (17138-28-2) → (2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester (267889-00-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: K₂CO₃ / dimethylformamide

2.1: NaOH / H₂O; methanol

3.1: DCC; HOBt

4.1: LAH

5.1: 82 percent / n-BuLi

6.1: 51 percent / LDA

7.1: H₂ / Pd/C

7.2: ethyl acetate / reflux

8.1: DMAP

9.1: P₄S₁₀; NaHCO₃

10.1: TsOH / methanol

11.1: Et₃N

12.1: 90 percent / K₂CO₃ / methanol / 0.5 h

With dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; tetraphosphorus decasulfide; hydrogen; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Acylation / 4.1: Reduction / 5.1: Addition / 6.1: Addition / 6.2: Addition / 7.1: Hydrogenolysis / 7.2: Cyclization / 8.1: silylation / 9.1: sulfuration / 10.1: desilylation / 11.1: silylation / 12.1: Isomerization;

DOI:10.1016/S0040-4039(00)00096-4

upstream raw materials:

(2S,3R,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester

2-[4-(benzyloxy)benzyl]acetic acid

(4-hydroxy-phenyl)-acetic acid ethyl ester

2-<4-(phenylmethoxy)phenyl>acetic acid ethyl ester

Downstream raw materials:

(2S,3S,4R)-plakoridine A

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