(4aR,6aS,7R,9aR,9bS)-toluene-4-sulfonic acid 9a-hydroxy-6a-methyl-3-oxododecahydrocyclopenta[h]isochromen-7-yl ester

Base Information

Chemical Name:(4aR,6aS,7R,9aR,9bS)-toluene-4-sulfonic acid 9a-hydroxy-6a-methyl-3-oxododecahydrocyclopenta[h]isochromen-7-yl ester
CAS No.:320594-06-7
Molecular Formula:C₂₀H₂₆O₆S
Molecular Weight:394.489
Hs Code.:

Synonyms:(4aR,6aS,7R,9aR,9bS)-toluene-4-sulfonic acid 9a-hydroxy-6a-methyl-3-oxododecahydrocyclopenta[h]isochromen-7-yl ester

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Chemical Property of (4aR,6aS,7R,9aR,9bS)-toluene-4-sulfonic acid 9a-hydroxy-6a-methyl-3-oxododecahydrocyclopenta[h]isochromen-7-yl ester

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Technology Process of (4aR,6aS,7R,9aR,9bS)-toluene-4-sulfonic acid 9a-hydroxy-6a-methyl-3-oxododecahydrocyclopenta[h]isochromen-7-yl ester

There total 7 articles about (4aR,6aS,7R,9aR,9bS)-toluene-4-sulfonic acid 9a-hydroxy-6a-methyl-3-oxododecahydrocyclopenta[h]isochromen-7-yl 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: 92.0%

: 98-59-9
p-toluenesulfonyl chloride

: 320594-07-8
(4aR,6aS,7R,9aR,9bS)-7,9a-dihydroxy-6a-methyldecahydrocyclopenta[h]isochromen-3(1H)-one

: 320594-06-7
(4aR,6aS,7R,9aR,9bS)-toluene-4-sulfonic acid 9a-hydroxy-6a-methyl-3-oxododecahydrocyclopenta[h]isochromen-7-yl ester

Guidance literature:: With pyridine; In chloroform; at 20 ℃; for 67h;
DOI:10.1021/jo005582h

Reference yield:

: 168130-61-8
(1R,3aR,4S,5R,7aS)-1-(tert-butyldimethylsilanyloxy)-5-(2,2-dimethoxyethyl)-3a-hydroxy-7a-methyloctahydroindene-4-carbonitrile

: 320594-06-7
(4aR,6aS,7R,9aR,9bS)-toluene-4-sulfonic acid 9a-hydroxy-6a-methyl-3-oxododecahydrocyclopenta[h]isochromen-7-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / imidazole; DMAP / CH₂Cl₂ / 24 h

2.1: 76 percent / DIBALH / hexane / -60 - 20 °C

3.1: 89 percent / NaBH₄ / ethanol / 1.5 h / -10 °C

4.1: aq. HCl / tetrahydrofuran / 96 h

4.2: 61 percent / Ag₂CO₃ on Celite / benzene / 6 h / Heating

5.1: 92 percent / pyridine / CHCl₃ / 67 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform;
DOI:10.1021/jo005582h

Reference yield:

: 168130-60-7
(1R,3aR,4R,5R,7aS)-1-(tert-butyldimethylsilanyloxy)-5-(2,2-dimethoxyethyl)-3a-hydroxy-7a-methyloctahydroindene-4-carbonitrile

: 320594-06-7
(4aR,6aS,7R,9aR,9bS)-toluene-4-sulfonic acid 9a-hydroxy-6a-methyl-3-oxododecahydrocyclopenta[h]isochromen-7-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 69 percent / aq. KOH / ethanol / 2 h / 50 °C

2.1: 99 percent / imidazole; DMAP / CH₂Cl₂ / 24 h

3.1: 76 percent / DIBALH / hexane / -60 - 20 °C

4.1: 89 percent / NaBH₄ / ethanol / 1.5 h / -10 °C

5.1: aq. HCl / tetrahydrofuran / 96 h

5.2: 61 percent / Ag₂CO₃ on Celite / benzene / 6 h / Heating

6.1: 92 percent / pyridine / CHCl₃ / 67 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; potassium hydroxide; sodium tetrahydroborate; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform;
DOI:10.1021/jo005582h