Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2R,5R,2'R)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester

Base Information

• Chemical Name: Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2R,5R,2'R)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester
• CAS No.: 862558-37-0
• Molecular Formula: C₂₄H₃₄O₇S
• Molecular Weight: 466.596
• Mol file: 862558-37-0.mol

Synonyms:Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2R,5R,2'R)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester

Chemical Property of Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2R,5R,2'R)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2R,5R,2'R)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester

There total 7 articles about Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2R,5R,2'R)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester 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:

((E)-8-Iodo-oct-4-enyloxymethyl)-benzene (862558-02-9) → Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2R,5R,2'R)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester (862558-37-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / NaHCO₃ / acetonitrile / 8 h / Heating

2.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

2.2: HMPA / tetrahydrofuran / 3.5 h / -78 - 0 °C

3.1: TBAF / tetrahydrofuran / 4 h

4.1: 85 percent / TFAA; Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 20 °C

5.1: triethylamine

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydrogencarbonate; rhenium(VII) oxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; acetonitrile; 2.2: Wittig reaction;

DOI:10.1021/jo050697c

Reference yield:

(R)-5-((4Z,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one (862556-98-7) → Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2R,5R,2'R)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester (862558-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / TFAA; Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 20 °C

2: triethylamine

With 2,6-dimethylpyridine; rhenium(VII) oxide; triethylamine; trifluoroacetic anhydride; In dichloromethane;

DOI:10.1021/jo050697c

Reference yield:

(R)-5-[(4Z,8E)-(R)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one (862557-78-6) → Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2R,5R,2'R)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester (862558-37-0)

Guidance literature:

Multi-step reaction with 3 steps

1: TBAF / tetrahydrofuran / 4 h

2: 85 percent / TFAA; Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 20 °C

3: triethylamine

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; rhenium(VII) oxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo050697c

upstream raw materials:

(2R,2'R,5'R)-5'-((E)-(S)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one

methanesulfonyl chloride

((E)-8-Iodo-oct-4-enyloxymethyl)-benzene

(R)-5-((4Z,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one

Downstream raw materials:

(2R,2'R,5'R,2''R,5''R)-5''-((R)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one