(2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-2a,5-dimethyl-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl ester

Base Information

• Chemical Name: (2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-2a,5-dimethyl-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl ester
• CAS No.: 115678-42-7
• Molecular Formula: C₂₇H₄₀O₅SSi
• Molecular Weight: 504.763

Synonyms:(2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-2a,5-dimethyl-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl ester

Chemical Property of (2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-2a,5-dimethyl-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-2a,5-dimethyl-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl ester

There total 7 articles about (2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-2a,5-dimethyl-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl 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%

(2aR,3aS,5R,6aS,7aR)-6a-Benzenesulfonyl-2a,5-dimethyl-7-oxo-decahydro-cyclobuta[f]indene-5-carboxylic acid methyl ester (114430-20-5,115792-80-8,115792-81-9) + tert-butyldimethylsilyl chloride (18162-48-6) → (2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-2a,5-dimethyl-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl ester (115678-42-7)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; toluene; benzene; 1.) -70 deg C, 40 min; 2.) 5 deg C, 40 min;

DOI:10.1021/ja00225a037

Reference yield:

(E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane (58274-64-9,82223-93-6,73912-36-4) → (2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-2a,5-dimethyl-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl ester (115678-42-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 2,6-di-tert-butyl-4-methylphenol; 2.) Jones reagent / 1.) 145 deg C, 5 d; 2.) acetone, 0 deg C, 10 min

2: 71 percent / CH₂Cl₂ / 4 h / Irradiation

3: 95 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene; benzene / 1.) -70 deg C, 40 min; 2.) 5 deg C, 40 min

With jones reagent; 2,6-di-tert-butyl-4-methyl-phenol; potassium hexamethylsilazane; In tetrahydrofuran; dichloromethane; toluene; benzene;

DOI:10.1021/ja00225a037

Reference yield:

methyl 1-(phenylsulfonyl)-4-methylcyclopentene-4-carboxylate (115678-58-5) → (2aS,3aR,5S,6aR)-6a-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-2a,5-dimethyl-2,2a,3,3a,4,5,6,6a-octahydro-1H-cyclobuta[f]indene-5-carboxylic acid methyl ester (115678-42-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 2,6-di-tert-butyl-4-methylphenol; 2.) Jones reagent / 1.) 145 deg C, 5 d; 2.) acetone, 0 deg C, 10 min

2: 71 percent / CH₂Cl₂ / 4 h / Irradiation

3: 95 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene; benzene / 1.) -70 deg C, 40 min; 2.) 5 deg C, 40 min

With jones reagent; 2,6-di-tert-butyl-4-methyl-phenol; potassium hexamethylsilazane; In tetrahydrofuran; dichloromethane; toluene; benzene;

DOI:10.1021/ja00225a037

upstream raw materials:

(2aR,3aS,5R,6aS,7aR)-6a-Benzenesulfonyl-2a,5-dimethyl-7-oxo-decahydro-cyclobuta[f]indene-5-carboxylic acid methyl ester

tert-butyldimethylsilyl chloride

(E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane

phenylselenyl benzenesulfonate

Downstream raw materials:

(2aS,3aS,5R,6aS,7aR)-3a-Benzenesulfonyl-2a-(tert-butyl-dimethyl-silanyloxy)-5,7a-dimethyl-3-oxo-decahydro-cyclobuta[f]indene-5-carboxylic acid methyl ester

C₂₈H₄₃NO₆S₂Si

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