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

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Chemical Name:(2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-5-[2-oxo-octadec-(E)-ylidene]-2-propyl-pyrrolidine-3-carboxylic acid methyl ester
CAS No.:267889-01-0
Molecular Formula:C₅₁H₇₅NO₅Si
Molecular Weight:810.246
Hs Code.:

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

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

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

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Technology Process of (2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-5-[2-oxo-octadec-(E)-ylidene]-2-propyl-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-5-[2-oxo-octadec-(E)-ylidene]-2-propyl-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:

: 6547-53-1
2-[4-(benzyloxy)benzyl]acetic acid

: 267889-01-0
(2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-5-[2-oxo-octadec-(E)-ylidene]-2-propyl-pyrrolidine-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 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

11.1: CH₂Cl₂

12.1: PPh₃; Et₃N

With dmap; lithium aluminium tetrahydride; n-butyllithium; tetraphosphorus decasulfide; hydrogen; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane; 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 / 11.1: Alkylation / 12.1: Alkylation;
DOI:10.1016/S0040-4039(00)00096-4

Reference yield:

: 17138-28-2
(4-hydroxy-phenyl)-acetic acid ethyl ester

: 267889-01-0
(2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-5-[2-oxo-octadec-(E)-ylidene]-2-propyl-pyrrolidine-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 14 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

13.1: CH₂Cl₂

14.1: PPh₃; Et₃N

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; triphenylphosphine; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane; 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 / 13.1: Alkylation / 14.1: Alkylation;
DOI:10.1016/S0040-4039(00)00096-4

Reference yield:

: 56441-69-1
2-<4-(phenylmethoxy)phenyl>acetic acid ethyl ester

: 267889-01-0
(2S,3S,4R)-1-{2-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-ethyl}-4-hydroxy-5-[2-oxo-octadec-(E)-ylidene]-2-propyl-pyrrolidine-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: NaOH / H₂O; methanol

2.1: DCC; HOBt

3.1: LAH

4.1: 82 percent / n-BuLi

5.1: 51 percent / LDA

6.1: H₂ / Pd/C

6.2: ethyl acetate / reflux

7.1: DMAP

8.1: P₄S₁₀; NaHCO₃

9.1: TsOH / methanol

10.1: Et₃N

11.1: 90 percent / K₂CO₃ / methanol / 0.5 h

12.1: CH₂Cl₂

13.1: PPh₃; Et₃N

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; triphenylphosphine; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane; water; 1.1: Hydrolysis / 2.1: Acylation / 3.1: Reduction / 4.1: Addition / 5.1: Addition / 5.2: Addition / 6.1: Hydrogenolysis / 6.2: Cyclization / 7.1: silylation / 8.1: sulfuration / 9.1: desilylation / 10.1: silylation / 11.1: Isomerization / 12.1: Alkylation / 13.1: Alkylation;
DOI:10.1016/S0040-4039(00)00096-4