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

Base Information

• Chemical Name: (3R,3aS,8R,10aS)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-3a-methyl-3a,4,7,8-tetrahydro-2H-8,10a-epoxycyclohepta[e]-inden-6(3H)-one
• CAS No.: 1287695-79-7
• Molecular Formula: C₄₁H₅₆O₄Si₂
• Molecular Weight: 669.064

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

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

Chemical Property:

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

There total 9 articles about (3R,3aS,8R,10aS)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-3a-methyl-3a,4,7,8-tetrahydro-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: 90.0%

(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 (1287695-78-6) → (3R,3aS,8R,10aS)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-3a-methyl-3a,4,7,8-tetrahydro-2H-8,10a-epoxycyclohepta[e]-inden-6(3H)-one (1287695-79-7)

Guidance literature:

With florisil; In toluene; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.201502890

Reference yield:

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 (1287695-76-4) → (3R,3aS,8R,10aS)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-3a-methyl-3a,4,7,8-tetrahydro-2H-8,10a-epoxycyclohepta[e]-inden-6(3H)-one (1287695-79-7)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: Florisil / benzene / 60 °C / Inert atmosphere

With triethylsilyl trifluoromethyl sulfonate; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; benzene;

DOI:10.1039/c1cc00087j

Reference yield:

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 (1287695-77-5) → (3R,3aS,8R,10aS)-3-(tert-butyldimethylsiloxy)-8-(4-(tert-butyldiphenylsiloxy)butyl)-3a-methyl-3a,4,7,8-tetrahydro-2H-8,10a-epoxycyclohepta[e]-inden-6(3H)-one (1287695-79-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: Florisil / benzene / 60 °C / Inert atmosphere

With triethylsilyl trifluoromethyl sulfonate; In dichloromethane; benzene;

DOI:10.1039/c1cc00087j

upstream raw materials:

(1S,2R,3R)-2-allyl-3-(tert-butyldimethylsiloxy)-1-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-2-methylcyclopentanol

(((1R,2S)-2-allyl-3-(5-(4-(tert-butyldiphenylsiloxy)butyl)furan-2-yl)-2-methyl-cyclopent-3-en-1-yl)oxy)(tert-butyl)dimethylsilane

(E)-5-((1S,5R)-5-(tert-butyldimethylsilyloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)pent-3-en-2-one

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

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