(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine

Base Information

• Chemical Name: (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine
• CAS No.: 316139-42-1
• Molecular Formula: C₂₆H₄₃NO₆Si
• Molecular Weight: 493.716

Synonyms:(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine

Chemical Property of (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine

Chemical Property:

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Technology Process of (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine

There total 1 articles about (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine 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: 92.0%

(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-chloroacetoxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine (316139-44-3) → (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine (316139-42-1)

Guidance literature:

With ammonium hydroxide; In ethanol; at 15 ℃; for 0.5h;

DOI:10.1016/S0957-4166(00)00326-8

Reference yield: 90.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine (316139-42-1) → (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{4-[(S)-2-ethoxycarbonyl-1-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-ethyl]-phenyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0957-4166(00)00326-8

Reference yield:

(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-hydroxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine (316139-42-1) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-{4-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-phenyl}-2-ethoxycarbonyl-ethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

2: 51 percent / TFA / CH₂Cl₂ / 2.5 h / 0 - 20 °C

With dmap; trifluoroacetic acid; In dichloromethane; 1: Acylation / 2: deacylation;

DOI:10.1016/S0957-4166(00)00326-8

upstream raw materials:

(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[4-((S)-1-chloroacetoxy-2-(ethoxycarbonyl)ethyl)phenyl]pyrrolidine

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