Toluene-4-sulfonic acid (3'aS,4'R,7'aR)-7'a-methyl-5'-oxo-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (3'aS,4'R,7'aR)-7'a-methyl-5'-oxo-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester
• CAS No.: 276244-57-6
• Molecular Formula: C₂₀H₂₆O₆S
• Molecular Weight: 394.489
• Mol file: 276244-57-6.mol

Synonyms:Toluene-4-sulfonic acid (3'aS,4'R,7'aR)-7'a-methyl-5'-oxo-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (3'aS,4'R,7'aR)-7'a-methyl-5'-oxo-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (3'aS,4'R,7'aR)-7'a-methyl-5'-oxo-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester

There total 5 articles about Toluene-4-sulfonic acid (3'aS,4'R,7'aR)-7'a-methyl-5'-oxo-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl 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: 98.0%

Toluene-4-sulfonic acid (3'aS,4'R,5'S,7'aR)-5'-hydroxy-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester (276244-56-5) → Toluene-4-sulfonic acid (3'aS,4'R,7'aR)-7'a-methyl-5'-oxo-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester (276244-57-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 0.5h;

DOI:10.1021/ja992491x

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (3'aS,4'R,7'aR)-7'a-methyl-5'-oxo-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester (276244-57-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / pyridine; DMAP / CH₂Cl₂ / 20 °C

2: 46 mg / triethyl orthoformate; TsOH / CH₂Cl₂ / 20 °C

3: 98 percent / Dess-Martin periodinate / CH₂Cl₂ / 0.5 h

With pyridine; dmap; Dess-Martin periodane; toluene-4-sulfonic acid; orthoformic acid triethyl ester; In dichloromethane; 1: Tosylation / 2: ketalization / 3: Oxidation;

DOI:10.1021/ja992491x

Reference yield:

(3aR,6S,7R,7aS)-6-Hydroxy-7-hydroxymethyl-3a-methyl-octahydro-inden-2-one (276244-55-4) → Toluene-4-sulfonic acid (3'aS,4'R,7'aR)-7'a-methyl-5'-oxo-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester (276244-57-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / pyridine; DMAP / CH₂Cl₂ / 20 °C

2: 46 mg / triethyl orthoformate; TsOH / CH₂Cl₂ / 20 °C

3: 98 percent / Dess-Martin periodinate / CH₂Cl₂ / 0.5 h

With pyridine; dmap; Dess-Martin periodane; toluene-4-sulfonic acid; orthoformic acid triethyl ester; In dichloromethane; 1: Tosylation / 2: ketalization / 3: Oxidation;

DOI:10.1021/ja992491x

upstream raw materials:

Toluene-4-sulfonic acid (3'aS,4'R,5'S,7'aR)-5'-hydroxy-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester

p-toluenesulfonyl chloride

(3aR,6S,7R,7aS)-6-Hydroxy-7-hydroxymethyl-3a-methyl-octahydro-inden-2-one

Toluene-4-sulfonic acid (3aS,4R,5S,7aR)-5-hydroxy-7a-methyl-2-oxo-octahydro-inden-4-ylmethyl ester

Downstream raw materials:

Androst-4-en-3,16-dion