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

Base Information

Chemical Name: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
CAS No.:444926-40-3
Molecular Formula:C₂₀H₂₈O₇S
Molecular Weight:412.504
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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: 89.0%

: 444926-51-6
(3'aS,4'R,5'S,7'aS)-4'-Benzenesulfonyloxymethyl-5'-hydroxy-7'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-indene]-1'-carboxylic acid ethyl ester

: 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

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h;
DOI:10.1021/jo020103v

Reference yield:

: 276244-50-9
C₂₁H₃₄O₃

: 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

Guidance literature:: Multi-step reaction with 5 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

With pyridine; 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

: 444926-40-3
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

Guidance literature:: Multi-step reaction with 4 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

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