(3R,3aS,5R,5aS,8R,10aR)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-5-hydroxy-3a-methyl-3a,4,5,5a,7,8-hexahydro-2H-8,10a-epoxycyclohepta[e]inden-6(3H)-one

Base Information

Chemical Name:(3R,3aS,5R,5aS,8R,10aR)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-5-hydroxy-3a-methyl-3a,4,5,5a,7,8-hexahydro-2H-8,10a-epoxycyclohepta[e]inden-6(3H)-one
CAS No.:1287695-78-6
Molecular Formula:C₄₁H₅₈O₅Si₂
Molecular Weight:687.08
Hs Code.:

(3R,3aS,5R,5aS,8R,10aR)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-5-hydroxy-3a-methyl-3a,4,5,5a,7,8-hexahydro-2H-8,10a-epoxycyclohepta[e]inden-6(3H)-one

Synonyms:(3R,3aS,5R,5aS,8R,10aR)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-5-hydroxy-3a-methyl-3a,4,5,5a,7,8-hexahydro-2H-8,10a-epoxycyclohepta[e]inden-6(3H)-one

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Chemical Property of (3R,3aS,5R,5aS,8R,10aR)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-5-hydroxy-3a-methyl-3a,4,5,5a,7,8-hexahydro-2H-8,10a-epoxycyclohepta[e]inden-6(3H)-one

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Technology Process of (3R,3aS,5R,5aS,8R,10aR)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-5-hydroxy-3a-methyl-3a,4,5,5a,7,8-hexahydro-2H-8,10a-epoxycyclohepta[e]inden-6(3H)-one

There total 9 articles about (3R,3aS,5R,5aS,8R,10aR)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-5-hydroxy-3a-methyl-3a,4,5,5a,7,8-hexahydro-2H-8,10a-epoxycyclohepta[e]inden-6(3H)-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: 87.0%

: 1287695-77-5
tert-butyl(4-(5-((4R,5S)-4-(tert-butyldimethylsiloxy)-5-methyl-5-(((2R,3S)-3-(1-(triethylsiloxy)vinyl)oxiran-2-yl)methyl)cyclopent-1-en-1-yl)furan-2-yl)butoxyl)diphenylsilane

: 1287695-78-6
(3R,3aS,5R,5aS,8R,10aR)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-5-hydroxy-3a-methyl-3a,4,5,5a,7,8-hexahydro-2H-8,10a-epoxycyclohepta[e]inden-6(3H)-one

Guidance literature:: With triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -78 ℃; for 1.5h; Inert atmosphere;
DOI:10.1039/c1cc00087j

Reference yield:

: 1287695-76-4
1-((2S,3R)-3-(((1S,5R)-5-(tert-butyldimethylsiloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)methyl)oxiran-2-yl)ethanone

: 1287695-78-6
(3R,3aS,5R,5aS,8R,10aR)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-5-hydroxy-3a-methyl-3a,4,5,5a,7,8-hexahydro-2H-8,10a-epoxycyclohepta[e]inden-6(3H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

2: triethylsilyl trifluoromethyl sulfonate / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

With triethylsilyl trifluoromethyl sulfonate; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1039/c1cc00087j

Reference yield:

: 1287695-82-2
(2R,3R)-2-allyl-3-(tert-butyldimethylsiloxy)-2-methylcyclopentanone

: 1287695-78-6
(3R,3aS,5R,5aS,8R,10aR)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-5-hydroxy-3a-methyl-3a,4,5,5a,7,8-hexahydro-2H-8,10a-epoxycyclohepta[e]inden-6(3H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 0 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 20 °C / Inert atmosphere

4.1: 9-epi-9-amino-9-deoxyquinine; Cumene hydroperoxide; trifluoroacetic acid / toluene / 20 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

6.1: triethylsilyl trifluoromethyl sulfonate / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

With 9-epi-9-amino-9-deoxyquinine; n-butyllithium; Hoveyda-Grubbs catalyst second generation; N,N,N,N,-tetramethylethylenediamine; Cumene hydroperoxide; triethylsilyl trifluoromethyl sulfonate; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1039/c1cc00087j