1,3-Dioxolane-4-ethanol, 5,5-diethyl-2,2-dimethyl-, 4-methylbenzenesulfonate, (S)-

Base Information

• Chemical Name: 1,3-Dioxolane-4-ethanol, 5,5-diethyl-2,2-dimethyl-, 4-methylbenzenesulfonate, (S)-
• CAS No.: 189102-20-3
• Molecular Formula: C₁₈H₂₈O₅S
• Molecular Weight: 356.483
• Mol file: 189102-20-3.mol

Synonyms:

Chemical Property of 1,3-Dioxolane-4-ethanol, 5,5-diethyl-2,2-dimethyl-, 4-methylbenzenesulfonate, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3-Dioxolane-4-ethanol, 5,5-diethyl-2,2-dimethyl-, 4-methylbenzenesulfonate, (S)-

There total 1 articles about 1,3-Dioxolane-4-ethanol, 5,5-diethyl-2,2-dimethyl-, 4-methylbenzenesulfonate, (S)- 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: 90.0%

p-toluenesulfonyl chloride (98-59-9) + 2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol → Toluene-4-sulfonic acid 2-((S)-5,5-diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (189102-20-3)

Guidance literature:

With pyridine;

DOI:10.1021/jo970049w

Reference yield:

Toluene-4-sulfonic acid 2-((S)-5,5-diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (189102-20-3) → (S)-4-Ethyl-1-((R)-1-{(1S,3aS,7aS)-4-[2-[(3S,5S)-5-hydroxy-3-hydroxymethyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-ethoxy)-hexane-3,4-diol

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) KH / 1.) THF, room temperature, 15 min, 2.) THF, reflux, 2.5 h.

2: tetrabutylammonium fluoride hydrate, molecular sieves 4 Angstroem / tetrahydrofuran / 1 h / Ambient temperature

3: 100 percent / tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

4: 1.) PhLi / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 5 h.

5: 25 percent / TBAF, molecular sieves 4 Angstroeme / tetrahydrofuran / 12 h / Ambient temperature

6: 67 percent / Dowex 50WX₄-200 / methanol / 17 h / Ambient temperature

With tetrapropylammonium perruthennate; 4 A molecular sieve; Dowex 50WX₄-200; tetrabutyl ammonium fluoride; potassium hydride; phenyllithium; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo970049w

Reference yield:

Toluene-4-sulfonic acid 2-((S)-5,5-diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (189102-20-3) → (1R,5R)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol (189102-64-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) KH / 1.) THF, room temperature, 15 min, 2.) THF, reflux, 2.5 h.

2: tetrabutylammonium fluoride hydrate, molecular sieves 4 Angstroem / tetrahydrofuran / 1 h / Ambient temperature

3: 100 percent / tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

4: 1.) PhLi / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 5 h.

5: 37 percent / TBAF, molecular sieves 4 Angstroeme / tetrahydrofuran / 12 h / Ambient temperature

With tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; potassium hydride; phenyllithium; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo970049w

upstream raw materials:

p-toluenesulfonyl chloride

Downstream raw materials:

(1R,5R)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

(1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

Refernces