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

Base Information

• Chemical Name: (2R,3S)-3-t-butyldimethylsilyloxy-2-phenylthio-1-(2-trimethylacetoxyethyl)pyrrolidin-5-one
• CAS No.: 119519-97-0
• Molecular Formula: C₂₃H₃₇NO₄SSi
• Molecular Weight: 451.703
• Mol file: 119519-97-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2R,3S)-3-t-butyldimethylsilyloxy-2-phenylthio-1-(2-trimethylacetoxyethyl)pyrrolidin-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: 98.5%

(2R,3S)-1-(2-hydroxyethyl)-3-t-butyldimethylsilyloxy-2-phenylthiopyrrolidin-5-one (119519-96-9) + pivaloyl chloride (3282-30-2) → (2R,3S)-3-t-butyldimethylsilyloxy-2-phenylthio-1-(2-trimethylacetoxyethyl)pyrrolidin-5-one (119519-97-0)

Guidance literature:

With pyridine; In diethyl ether; for 12h; Ambient temperature;

Reference yield:

(3S)-3-acetoxy-1-(2-benzoyloxyethyl)pyrrolidine-2,5-dione (119519-81-2) → (2R,3S)-3-t-butyldimethylsilyloxy-2-phenylthio-1-(2-trimethylacetoxyethyl)pyrrolidin-5-one (119519-97-0)

Guidance literature:

Multi-step reaction with 5 steps

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

2: toluene-p-sulphonic acid

4: K₂CO₃ / methanol

5: pyridine / diethyl ether

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

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)-3-t-butyldimethylsilyloxy-2-phenylthio-1-(2-trimethylacetoxyethyl)pyrrolidin-5-one (119519-97-0)

Guidance literature:

Multi-step reaction with 4 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

4: 98.5 percent / pyridine / diethyl ether / 12 h / Ambient temperature

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

upstream raw materials:

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

pivaloyl chloride

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

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

Downstream raw materials:

(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