(Z)-(4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,12,12a-hexahydro-4H-7-oxa-benzocyclodecene-1,6-dione

Base Information

Chemical Name:(Z)-(4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,12,12a-hexahydro-4H-7-oxa-benzocyclodecene-1,6-dione
CAS No.:864155-67-9
Molecular Formula:C₃₀H₃₆O₄Si
Molecular Weight:488.699
Hs Code.:

Synonyms:(Z)-(4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,12,12a-hexahydro-4H-7-oxa-benzocyclodecene-1,6-dione

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (Z)-(4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,12,12a-hexahydro-4H-7-oxa-benzocyclodecene-1,6-dione

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (Z)-(4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,12,12a-hexahydro-4H-7-oxa-benzocyclodecene-1,6-dione

There total 15 articles about (Z)-(4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,12,12a-hexahydro-4H-7-oxa-benzocyclodecene-1,6-dione 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: 95.0%

: 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

: 864155-67-9
(Z)-(4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,12,12a-hexahydro-4H-7-oxa-benzocyclodecene-1,6-dione

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 6h;
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

: 864155-67-9
(Z)-(4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,12,12a-hexahydro-4H-7-oxa-benzocyclodecene-1,6-dione

Guidance literature:: Multi-step reaction with 6 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

6: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 6 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; cerium(III) chloride; Dess-Martin periodane; 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

: 864155-67-9
(Z)-(4S,4aR,8S,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,12,12a-hexahydro-4H-7-oxa-benzocyclodecene-1,6-dione

Guidance literature:: Multi-step reaction with 5 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

5: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 6 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; Dess-Martin periodane; 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