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

Base Information

• Chemical Name: 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
• CAS No.: 82933-79-7
• Molecular Formula: C₃₆H₅₆O₇S₃
• Molecular Weight: 697.034
• Mol file: 82933-79-7.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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:

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) → 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 5 steps

1: 93 percent / pyridine / 22 h / 0 - 5 °C

2: 100 percent / LiBr, NaHCO₃ / dimethylformamide / 23 h / 25 °C

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

4: 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

5: 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

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 (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 6 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

3: 100 percent / LiBr, NaHCO₃ / dimethylformamide / 23 h / 25 °C

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

5: 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

6: pyridine / 22 h / 0 - 5 °C

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

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:

{(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]-cyclopentyl}-methanol

benzenesulfonyl chloride

C₂₆H₄₃BrO₄

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