(2R,3S)-1-(2-hydroxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one

Base Information

• Chemical Name: (2R,3S)-1-(2-hydroxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one
• CAS No.: 119519-96-9
• Molecular Formula: C₁₈H₂₉NO₃SSi
• Molecular Weight: 367.585
• Mol file: 119519-96-9.mol

Synonyms:(2R,3S)-1-(2-hydroxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one

Chemical Property of (2R,3S)-1-(2-hydroxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-(2-hydroxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one

There total 9 articles about (2R,3S)-1-(2-hydroxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one 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: 84.0%

(2R,3S)-1-(2-benzoyloxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one (119519-95-8) → (2R,3S)-1-(2-hydroxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one (119519-96-9)

Guidance literature:

With potassium carbonate; In methanol; for 1h; Ambient temperature;

Reference yield:

(3S)-3-acetoxy-1-(2-benzoyloxyethyl)pyrrolidine-2,5-dione (119519-81-2) → (2R,3S)-1-(2-hydroxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one (119519-96-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) sodium borohydride, 2.) HCl

2: toluene-p-sulphonic acid

4: K₂CO₃ / methanol

With hydrogenchloride; sodium tetrahydroborate; potassium carbonate; toluene-4-sulfonic acid; In methanol;

DOI:10.1039/c39880000685

Reference yield:

(2RS,3R)-3-acetoxy-1-(2-benzoyloxyethyl)-2-ethoxypyrrolidin-5-one (119519-82-3,128935-41-1,128935-55-7) → (2R,3S)-1-(2-hydroxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one (119519-96-9)

Guidance literature:

Multi-step reaction with 3 steps

1: p-TsOH / 2 h / Ambient temperature

2: 65.9 percent / NEt₃ / tetrahydrofuran / 5 h / Ambient temperature

3: 84 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

With potassium carbonate; triethylamine; toluene-4-sulfonic acid; In tetrahydrofuran; methanol;

upstream raw materials:

(2R,3S)-1-(2-benzoyloxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one

(3S)-3-acetoxy-1-(2-benzoyloxyethyl)pyrrolidine-2,5-dione

tert-butyldimethylsilyl chloride

(2RS,3R)-3-acetoxy-1-(2-benzoyloxyethyl)-2-ethoxypyrrolidin-5-one

Downstream raw materials:

(2R,3S)-3-t-butyldimethylsilyloxy-2-phenylthio-1-(2-trimethylacetoxyethyl)pyrrolidin-5-one

(2R,3S)-3-t-butyldimethylsilyloxy-2-bis(benzyloxycarbonyl)methyl-1-(2-trimethylacetoxyethyl)pyrrolidin-5-one

2-{(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-[2-(2,2-dimethyl-propionyloxy)-ethyl]-5-oxo-pyrrolidin-2-yl}-2-phenylsulfanyl-malonic acid dibenzyl ester