(5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

Base Information

• Chemical Name: (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one
• CAS No.: 628687-62-7
• Molecular Formula: C₂₈H₃₆O₅S
• Molecular Weight: 484.657
• Mol file: 628687-62-7.mol

Synonyms:(5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

Chemical Property of (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

There total 12 articles about (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-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: 67.0%

5S-(1S-hydroxyhex-5-ynyl)dihydrofuran-2-one (628687-56-9) + (5R)-3-(7-iodohept-6-enyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one (628687-57-0) → (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one (628687-62-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; for 24h;

DOI:10.1016/j.tetlet.2003.08.088

Reference yield:

8-(trimethylsilyl)-1-octen-7-yn-3-ol (66927-75-1) → (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one (628687-62-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / propionic acid / 2 h / 180 °C

2: 62 percent / AD-mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

3: 73 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 0 °C

4: 67 percent / Et₃N; CuI / Pd(PPh₃)2Cl₂ / 24 h / 20 °C

With AD-mix-α; copper(l) iodide; methanesulfonamide; tetrabutyl ammonium fluoride; propionic acid; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1016/j.bmc.2005.05.050

Reference yield:

(R)-5-methyl-3-phenylthio-3H-dihydrofuran-2-one (628687-61-6) → (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one (628687-62-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / 0 °C

1.2: 75 percent / hexamethylphosphoric triamide / tetrahydrofuran / 2 h / Heating

2.1: 67 percent / Et₃N; CuI / Pd(PPh₃)2Cl₂ / 24 h / 20 °C

With copper(l) iodide; triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran;

DOI:10.1016/j.bmc.2005.05.050

upstream raw materials:

5S-(1S-hydroxyhex-5-ynyl)dihydrofuran-2-one

(5R)-3-(7-iodohept-6-enyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

1-hydroxy-6-heptyne

8-(trimethylsilyl)-1-octen-7-yn-3-ol

Downstream raw materials:

(5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one