(+)-(3''S,3a''R,5''S,7a''S)-2''-phenylthio-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one

Base Information

Chemical Name:(+)-(3''S,3a''R,5''S,7a''S)-2''-phenylthio-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one
CAS No.:917097-46-2
Molecular Formula:C₂₇H₃₈O₃S
Molecular Weight:442.663
Hs Code.:

Synonyms:(+)-(3''S,3a''R,5''S,7a''S)-2''-phenylthio-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one

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Chemical Property of (+)-(3''S,3a''R,5''S,7a''S)-2''-phenylthio-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one

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Technology Process of (+)-(3''S,3a''R,5''S,7a''S)-2''-phenylthio-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one

There total 10 articles about (+)-(3''S,3a''R,5''S,7a''S)-2''-phenylthio-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one 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: 86.0%

: 917097-40-6
(+)-(3''S,3a''R,5''S,7a''S)-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one

: 1212-08-4
S-Phenyl benzenethiosulfonate

: 917097-46-2
(+)-(3''S,3a''R,5''S,7a''S)-2''-phenylthio-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one

Guidance literature:: (+)-(3''S,3a''R,5''S,7a''S)-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -70 ℃; for 1h;

S-Phenyl benzenethiosulfonate; In tetrahydrofuran; hexane; at -70 - 20 ℃; for 2h;
DOI:10.1021/ol062304h

Reference yield:

: 149789-99-1,126541-53-5
(1S,7aS)-1-((tert-butyldimethylsilyl)oxy)-7a-methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one

: 917097-46-2
(+)-(3''S,3a''R,5''S,7a''S)-2''-phenylthio-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / Heating

1.2: 16 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / 60 °C

2.1: 47 percent / TiCl₄; Mg / tetrahydrofuran / 0.75 h / 0 - 20 °C

3.1: 68 percent / TBAF / tetrahydrofuran / 1.5 h / 45 °C

4.1: 100 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

5.1: 95 percent / NaOMe / methanol / 20 °C

6.1: 85 percent / n-BuLi; CuCN / tetrahydrofuran; hexane / 2 h / -68 °C

7.1: 65 percent / H₂ / PtO₂ / methanol / 3 h / 20 °C

8.1: LDA / tetrahydrofuran; hexane / 1 h / -70 °C

8.2: 86 percent / tetrahydrofuran; hexane / 2 h / -70 - 20 °C

With pyridine; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; titanium tetrachloride; sodium hydride; Dess-Martin periodane; magnesium; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; 4.1: Dess-Martin oxidation;
DOI:10.1021/ol062304h

Reference yield:

: 917097-41-7
(+)-(3a''R,7a''S)-7a''-methyl-5''-methylene-5'',6'',7'',7a''-tetrahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(3a''H)-one

: 917097-46-2
(+)-(3''S,3a''R,5''S,7a''S)-2''-phenylthio-3''-isopropyl-5'',7a''-dimethyl-3'',3a'',5'',6'',7'',7a''-hexahydrodispiro[1,3-dioxolane-2,1'-cyclohexane-4',4''-inden]-1''(2''H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 85 percent / n-BuLi; CuCN / tetrahydrofuran; hexane / 2 h / -68 °C

2.1: 65 percent / H₂ / PtO₂ / methanol / 3 h / 20 °C

3.1: LDA / tetrahydrofuran; hexane / 1 h / -70 °C

3.2: 86 percent / tetrahydrofuran; hexane / 2 h / -70 - 20 °C

With n-butyllithium; hydrogen; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane;
DOI:10.1021/ol062304h