(3'aS,4'S,5'S,7'aS)-4'-[2-Benzenesulfonyl-2-(5-methoxy-2-methyl-phenyl)-ethyl]-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-5'-ol

Base Information

Chemical Name:(3'aS,4'S,5'S,7'aS)-4'-[2-Benzenesulfonyl-2-(5-methoxy-2-methyl-phenyl)-ethyl]-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-5'-ol
CAS No.:444926-58-3
Molecular Formula:C₂₉H₃₈O₇S
Molecular Weight:530.683
Hs Code.:

Synonyms:(3'aS,4'S,5'S,7'aS)-4'-[2-Benzenesulfonyl-2-(5-methoxy-2-methyl-phenyl)-ethyl]-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-5'-ol

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Chemical Property of (3'aS,4'S,5'S,7'aS)-4'-[2-Benzenesulfonyl-2-(5-methoxy-2-methyl-phenyl)-ethyl]-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-5'-ol

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Technology Process of (3'aS,4'S,5'S,7'aS)-4'-[2-Benzenesulfonyl-2-(5-methoxy-2-methyl-phenyl)-ethyl]-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-5'-ol

There total 9 articles about (3'aS,4'S,5'S,7'aS)-4'-[2-Benzenesulfonyl-2-(5-methoxy-2-methyl-phenyl)-ethyl]-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-5'-ol 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: 88.0%

: 444926-38-9
5-methoxy-2-methylbenzyl phenyl sulfone

: 444926-40-3
Benzenesulfonic acid (3'aS,4'R,5'S,7'aS)-5'-hydroxy-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester

: 444926-58-3
(3'aS,4'S,5'S,7'aS)-4'-[2-Benzenesulfonyl-2-(5-methoxy-2-methyl-phenyl)-ethyl]-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-5'-ol

Guidance literature:: 5-methoxy-2-methylbenzyl phenyl sulfone; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

Benzenesulfonic acid (3'aS,4'R,5'S,7'aS)-5'-hydroxy-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-4'-ylmethyl ester; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 7.5h; Further stages.;
DOI:10.1021/jo020103v

Reference yield:

: 276244-50-9
C₂₁H₃₄O₃

: 444926-58-3
(3'aS,4'S,5'S,7'aS)-4'-[2-Benzenesulfonyl-2-(5-methoxy-2-methyl-phenyl)-ethyl]-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-5'-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 14 percent Turnov_. / tetrahydrofuran / -78 - 20 °C

2.1: triethyl orthoformate; p-TsOH*H₂O / CH₂Cl₂ / 72 h / 20 °C

2.2: 18 percent / p-TsOH*H₂O / ethanol / 48 h / 20 °C

3.1: 86 percent / triethyl orthoformate; p-TsOH*H₂O / CH₂Cl₂ / 72 h / 20 °C

4.1: 86 percent Turnov_. / pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: 89 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 88 percent / tetrahydrofuran; hexane / 7.5 h / -78 - 20 °C

With pyridine; n-butyllithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; orthoformic acid triethyl ester; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo020103v

Reference yield:

: 444926-42-5
C₂₄H₃₈O₅

: 444926-58-3
(3'aS,4'S,5'S,7'aS)-4'-[2-Benzenesulfonyl-2-(5-methoxy-2-methyl-phenyl)-ethyl]-1'-hydroxymethyl-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-inden]-5'-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethyl orthoformate; p-TsOH*H₂O / CH₂Cl₂ / 72 h / 20 °C

1.2: 18 percent / p-TsOH*H₂O / ethanol / 48 h / 20 °C

2.1: 86 percent / triethyl orthoformate; p-TsOH*H₂O / CH₂Cl₂ / 72 h / 20 °C

3.1: 86 percent Turnov_. / pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 89 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 88 percent / tetrahydrofuran; hexane / 7.5 h / -78 - 20 °C

With pyridine; n-butyllithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; orthoformic acid triethyl ester; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo020103v