(3R,4R,5S)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one

Base Information

• Chemical Name: (3R,4R,5S)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one
• CAS No.: 1401240-50-3
• Molecular Formula: C₂₉H₂₉F₂NO₄S
• Molecular Weight: 525.616
• Mol file: 1401240-50-3.mol

Synonyms:(3R,4R,5S)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one

Chemical Property of (3R,4R,5S)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one

There total 7 articles about (3R,4R,5S)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-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: 40.0%

(3R,4R)-3,4-bis(benzyloxy)-1-(but-3-enyl)pyrrolidine-2,5-dione (127299-56-3) + phenyl (trimethylsilyl)difluoromethyl sulfide (536975-49-2) → (3R,4R,5R)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one (1401240-48-9) + (3R,4R,5S)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one (1401240-50-3)

Guidance literature:

With tetrabutylammonium triphenyldifluorosilicate; In N,N-dimethyl-formamide; at -78 ℃; for 10h;

DOI:10.1021/jo301327s

Reference yield:

diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate (77312-71-1) → (3R,4R,5R)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one (1401240-48-9) + (3R,4R,5S)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one (1401240-50-3)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium hydroxide monohydrate; water / ethanol / 24 h / 0 °C

2: acetyl chloride / 4 h / Reflux

3: dichloromethane / 5 h / 0 °C / Reflux

4: acetyl chloride / 5 h / Reflux

5: ammonium cerium (IV) nitrate / water; acetonitrile / 4 h / 0 - 20 °C

6: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran

7: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 10 h / -78 °C

With ammonium cerium (IV) nitrate; lithium hydroxide monohydrate; di-isopropyl azodicarboxylate; water; acetyl chloride; triphenylphosphine; tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo301327s

Reference yield:

(2R,3R)-2,3-bis(benzyloxy)tartaric acid (138794-81-7) → (3R,4R,5R)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one (1401240-48-9) + (3R,4R,5S)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one (1401240-50-3)

Guidance literature:

Multi-step reaction with 6 steps

1: acetyl chloride / 4 h / Reflux

2: dichloromethane / 5 h / 0 °C / Reflux

3: acetyl chloride / 5 h / Reflux

4: ammonium cerium (IV) nitrate / water; acetonitrile / 4 h / 0 - 20 °C

5: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran

6: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 10 h / -78 °C

With ammonium cerium (IV) nitrate; di-isopropyl azodicarboxylate; acetyl chloride; triphenylphosphine; tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo301327s

upstream raw materials:

diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate

(2R,3R)-2,3-bis(benzyloxy)tartaric acid

(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione

(3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione