(9R,9aS)-9-(3,4,5-Trimethoxy-phenyl)-9,9a-dihydro-1,5,7-trioxa-2-thia-cyclopenta[a]-s-indacene 2,2-dioxide

Base Information

Chemical Name:(9R,9aS)-9-(3,4,5-Trimethoxy-phenyl)-9,9a-dihydro-1,5,7-trioxa-2-thia-cyclopenta[a]-s-indacene 2,2-dioxide
CAS No.:94671-13-3
Molecular Formula:C₂₀H₁₈O₈S
Molecular Weight:418.424
Hs Code.:

Synonyms:(9R,9aS)-9-(3,4,5-Trimethoxy-phenyl)-9,9a-dihydro-1,5,7-trioxa-2-thia-cyclopenta[a]-s-indacene 2,2-dioxide

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Chemical Property of (9R,9aS)-9-(3,4,5-Trimethoxy-phenyl)-9,9a-dihydro-1,5,7-trioxa-2-thia-cyclopenta[a]-s-indacene 2,2-dioxide

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Technology Process of (9R,9aS)-9-(3,4,5-Trimethoxy-phenyl)-9,9a-dihydro-1,5,7-trioxa-2-thia-cyclopenta[a]-s-indacene 2,2-dioxide

There total 9 articles about (9R,9aS)-9-(3,4,5-Trimethoxy-phenyl)-9,9a-dihydro-1,5,7-trioxa-2-thia-cyclopenta[a]-s-indacene 2,2-dioxide 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: 55.0%

: 124-63-0
methanesulfonyl chloride

: 94671-11-1
trans-6,7-dihydro-6-hydroxy-7-(3,4,5-trimethoxyphenyl)-5H-indeno<5,6-d>-1,3-dioxol-5-one

: 94671-13-3
(9R,9aS)-9-(3,4,5-Trimethoxy-phenyl)-9,9a-dihydro-1,5,7-trioxa-2-thia-cyclopenta[a]-s-indacene 2,2-dioxide

: 94706-18-0
trans-6,7-dihydro-6-<(methylsulfonyl)oxy>-7-(3,4,5-trimethoxyphenyl)-5H-indeno<5,6-d>-1,3-dioxol-5-one

Guidance literature:: With triethylamine; In dichloromethane; at -10 ℃; for 0.5h;
DOI:10.1021/jo00207a034

Reference yield:

: 94671-17-7
7-(3,4,5-trimethoxyphenyl)-5H-indeno<5,6-d>-1,3-dioxole-5,6-dione 6-oxime

: 94671-13-3
(9R,9aS)-9-(3,4,5-Trimethoxy-phenyl)-9,9a-dihydro-1,5,7-trioxa-2-thia-cyclopenta[a]-s-indacene 2,2-dioxide

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / 1N KOH, concd. NH₄OH, 5percent NaOCl / 11 h / 0 - 25 °C

2: 8 percent / 5 h / Irradiation; var. solvents as reagents, var. reaction conditions

3: 1.) LDA, 2.) Et₃N / 1.) THF, -78 deg C, 0.5 h, 2.) from -78 deg C to 25 deg C, overnight

4: 24 percent / 5percent aq. NaHCO₃, m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

5: 45 percent / Et₃N / CH₂Cl₂ / 0.5 h / -10 °C

With potassium hydroxide; ammonium hydroxide; sodium hypochlorite; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In dichloromethane;
DOI:10.1021/jo00207a034

Reference yield:

: 94671-18-8
6-diazo-7-(3,4,5-trimethoxyphenyl)-5H-indeno<5,6-d>-1,3-dioxol-5-one

: 94671-13-3
(9R,9aS)-9-(3,4,5-Trimethoxy-phenyl)-9,9a-dihydro-1,5,7-trioxa-2-thia-cyclopenta[a]-s-indacene 2,2-dioxide

Guidance literature:: Multi-step reaction with 4 steps

1: 8 percent / 5 h / Irradiation; var. solvents as reagents, var. reaction conditions

2: 1.) LDA, 2.) Et₃N / 1.) THF, -78 deg C, 0.5 h, 2.) from -78 deg C to 25 deg C, overnight

3: 24 percent / 5percent aq. NaHCO₃, m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

4: 45 percent / Et₃N / CH₂Cl₂ / 0.5 h / -10 °C

With sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In dichloromethane;
DOI:10.1021/jo00207a034