(Z)-(1R,4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,12,12a-octahydro-7-oxa-benzocyclodecen-6-one

Base Information

Chemical Name:(Z)-(1R,4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,12,12a-octahydro-7-oxa-benzocyclodecen-6-one
CAS No.:864155-70-4
Molecular Formula:C₃₀H₃₈O₄Si
Molecular Weight:490.715
Hs Code.:

Synonyms:(Z)-(1R,4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,12,12a-octahydro-7-oxa-benzocyclodecen-6-one

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Chemical Property of (Z)-(1R,4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,12,12a-octahydro-7-oxa-benzocyclodecen-6-one

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Technology Process of (Z)-(1R,4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,12,12a-octahydro-7-oxa-benzocyclodecen-6-one

There total 14 articles about (Z)-(1R,4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,12,12a-octahydro-7-oxa-benzocyclodecen-6-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: 94.0%

: 864155-66-8
(Z)-(1R,4S,4aR,8S,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,12,12a-octahydro-7-oxa-benzocyclodecen-6-one

: 864155-70-4
(Z)-(1R,4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,12,12a-octahydro-7-oxa-benzocyclodecen-6-one

Guidance literature:: dichloro bis(acetonitrile) palladium(II); In water; acetone; at 20 ℃; for 5h;
DOI:10.1039/b505264e

Reference yield:

: 864155-61-3
[(1R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester

: 864155-70-4
(Z)-(1R,4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,12,12a-octahydro-7-oxa-benzocyclodecen-6-one

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄; CeCl₃ / methanol / 0.25 h / -50 °C

2: 93 percent / imidazole; DMAP / dimethylformamide

3: 91 percent / Ti(OiPr)4 / 90 °C

4: 84 percent / PhCH=Ru{[(Mes)NCH₂CH₂N(Mes)]CH}(PCy₃)Cl₂ / CH₂Cl₂ / 2 h / Heating

5: 94 percent / PdCl₂(CH₃CN)2 / acetone; H₂O / 5 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; cerium(III) chloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dichloro bis(acetonitrile) palladium(II); In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1: Luche reduction;
DOI:10.1039/b505264e

Reference yield:

: 864155-63-5
[(1R,2S,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

: 864155-70-4
(Z)-(1R,4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,12,12a-octahydro-7-oxa-benzocyclodecen-6-one

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / imidazole; DMAP / dimethylformamide

2: 91 percent / Ti(OiPr)4 / 90 °C

3: 84 percent / PhCH=Ru{[(Mes)NCH₂CH₂N(Mes)]CH}(PCy₃)Cl₂ / CH₂Cl₂ / 2 h / Heating

4: 94 percent / PdCl₂(CH₃CN)2 / acetone; H₂O / 5 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dichloro bis(acetonitrile) palladium(II); In dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1039/b505264e