3a-Benzenesulfonyl-9a-hydroxy-2,3,3a,4,5,8,9,9a-octahydro-1H-cyclopenta[b]naphthalene-6,7-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: 3a-Benzenesulfonyl-9a-hydroxy-2,3,3a,4,5,8,9,9a-octahydro-1H-cyclopenta[b]naphthalene-6,7-dicarboxylic acid dimethyl ester
• CAS No.: 86477-26-1
• Molecular Formula: C₂₃H₂₆O₇S
• Molecular Weight: 446.521
• Mol file: 86477-26-1.mol

Synonyms:

Chemical Property of 3a-Benzenesulfonyl-9a-hydroxy-2,3,3a,4,5,8,9,9a-octahydro-1H-cyclopenta[b]naphthalene-6,7-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3a-Benzenesulfonyl-9a-hydroxy-2,3,3a,4,5,8,9,9a-octahydro-1H-cyclopenta[b]naphthalene-6,7-dicarboxylic acid dimethyl ester

There total 5 articles about 3a-Benzenesulfonyl-9a-hydroxy-2,3,3a,4,5,8,9,9a-octahydro-1H-cyclopenta[b]naphthalene-6,7-dicarboxylic acid dimethyl 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: 95.0%

7a-Benzenesulfonyl-5,6-dimethylene-octahydro-inden-3a-ol (86477-23-8) + dimethyl acetylenedicarboxylate (762-42-5) → 3a-Benzenesulfonyl-9a-hydroxy-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-6,7-dicarboxylic acid dimethyl ester (86477-27-2) + 3a-Benzenesulfonyl-9a-hydroxy-2,3,3a,4,5,8,9,9a-octahydro-1H-cyclopenta[b]naphthalene-6,7-dicarboxylic acid dimethyl ester (86477-26-1)

Guidance literature:

In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(00)86383-2

Reference yield:

2-bromomethyl-3-(trimethylsilylmethyl)-buta-1,3-diene (86477-19-2) → 3a-Benzenesulfonyl-9a-hydroxy-2,3,3a,4,5,8,9,9a-octahydro-1H-cyclopenta[b]naphthalene-6,7-dicarboxylic acid dimethyl ester (86477-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH or KH / 1,2-dimethoxy-ethane / Heating

2: tetra-n-butylammonium fluoride / tetrahydrofuran / 55 °C

3: 95 percent / tetrahydrofuran / Heating

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane;

DOI:10.1016/S0040-4039(00)86383-2

Reference yield:

2-Benzenesulfonyl-2-(2-methylene-3-trimethylsilanylmethyl-but-3-enyl)-cyclopentanone (86477-20-5) → 3a-Benzenesulfonyl-9a-hydroxy-2,3,3a,4,5,8,9,9a-octahydro-1H-cyclopenta[b]naphthalene-6,7-dicarboxylic acid dimethyl ester (86477-26-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tetra-n-butylammonium fluoride / tetrahydrofuran / 55 °C

2: 95 percent / tetrahydrofuran / Heating

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86383-2

upstream raw materials:

7a-Benzenesulfonyl-5,6-dimethylene-octahydro-inden-3a-ol

dimethyl acetylenedicarboxylate

2-bromomethyl-3-(trimethylsilylmethyl)-buta-1,3-diene

2-Benzenesulfonyl-2-(2-methylene-3-trimethylsilanylmethyl-but-3-enyl)-cyclopentanone

Downstream raw materials:

5a-Benzenesulfonyl-9a-hydroxy-2-phenyl-3a,4,5,5a,6,7,8,9,9a,10,11,11a-dodecahydro-naphtho[2,3-f]isoindole-1,3-dione