Benzenesulfonic acid 2-{(1S,2S,3S)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester

Base Information

• Chemical Name: Benzenesulfonic acid 2-{(1S,2S,3S)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester
• CAS No.: 82933-76-4
• Molecular Formula: C₃₂H₄₈O₇S
• Molecular Weight: 576.795
• Mol file: 82933-76-4.mol

Synonyms:Benzenesulfonic acid 2-{(1S,2S,3S)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester

Chemical Property of Benzenesulfonic acid 2-{(1S,2S,3S)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzenesulfonic acid 2-{(1S,2S,3S)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester

There total 2 articles about Benzenesulfonic acid 2-{(1S,2S,3S)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl 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: 93.0%

2-{(1R,2R,3R)-5-Methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethanol (82933-75-3) + benzenesulfonyl chloride (98-09-9) → Benzenesulfonic acid 2-{(1S,2S,3S)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester (82933-76-4)

Guidance literature:

With pyridine; at 0 - 5 ℃; for 22h;

DOI:10.1021/jo00143a027

Reference yield:

tert-Butyl-dimethyl-(2-{(1R,2R,3R)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethoxy)-silane (82933-74-2) → Benzenesulfonic acid 2-{(1S,2S,3S)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester (82933-76-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / 0.75 M tetra-n-butylammonium fluoride / tetrahydrofuran / 18 h / Ambient temperature

2: 93 percent / pyridine / 22 h / 0 - 5 °C

With pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jo00143a027

Reference yield:

Benzenesulfonic acid 2-{(1S,2S,3S)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester (82933-76-4) → Benzenesulfonic acid (1S,2S,3R,4R)-2-(2-[1,3]dithian-2-yl-ethyl)-4-(tetrahydro-pyran-2-yloxy)-3-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentylmethyl ester (82933-79-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / LiBr, NaHCO₃ / dimethylformamide / 23 h / 25 °C

2: 1.) n-BuLi / 1.) THF, hexane, -20 deg C, 2h, 2.) -20 deg C, 2.5 h

3: 1.) 0.5 M 9-borobicyclo<3.3.2>nonane, 2.) 30percent H₂O₂, 3 N NaOH / 1.) THF, from 0 to 5 deg C, 3.5 h, 2.) 25 deg C, 15 min

4: pyridine / 22 h / 0 - 5 °C

With pyridine; sodium hydroxide; n-butyllithium; 9-borobicyclo<3.3.2>nonane; dihydrogen peroxide; sodium hydrogencarbonate; lithium bromide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00143a027

upstream raw materials:

2-{(1R,2R,3R)-5-Methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethanol

benzenesulfonyl chloride

tert-Butyl-dimethyl-(2-{(1R,2R,3R)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethoxy)-silane

Downstream raw materials:

Benzenesulfonic acid (1S,2S,3R,4R)-2-(2-[1,3]dithian-2-yl-ethyl)-4-(tetrahydro-pyran-2-yloxy)-3-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentylmethyl ester