(4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-4H-7-oxa-benzocyclodecene-1,6-dione

Base Information

Chemical Name:(4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-4H-7-oxa-benzocyclodecene-1,6-dione
CAS No.:883746-93-8
Molecular Formula:C₃₀H₃₈O₄Si
Molecular Weight:490.715
Hs Code.:

Synonyms:(4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-4H-7-oxa-benzocyclodecene-1,6-dione

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Chemical Property of (4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-4H-7-oxa-benzocyclodecene-1,6-dione

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Technology Process of (4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-4H-7-oxa-benzocyclodecene-1,6-dione

There total 8 articles about (4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-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: 92.0%

: 866430-89-9
(1R,4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one

: 883746-93-8
(4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-4H-7-oxa-benzocyclodecene-1,6-dione

Guidance literature:: With dipyridinium dichromate; 4 Angstroem MS; In dichloromethane; for 5h;
DOI:10.1016/j.tetlet.2005.07.152

Reference yield:

: 866430-79-7
[(1R,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester

: 883746-93-8
(4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-4H-7-oxa-benzocyclodecene-1,6-dione

Guidance literature:: Multi-step reaction with 7 steps

1: NaBH₄; CeCl₃ / methanol / -50 °C

2: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

3: 83 percent / Ti(OiPr)4 / 10 h / 90 °C

4: 30 percent / Ti(OiPr)4 / (PCy₃)2(Cl)2Ru=CHPh / benzene / 2 h / 80 °C

5: 77 percent / H₂ / (Ph₃P)3RhCl / 45 h / 760 Torr

6: 81 percent / PPTS / ethanol / 12 h

7: 92 percent / PDC; 4 Angstroem MS / CH₂Cl₂ / 5 h

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; 4 Angstroem MS; hydrogen; pyridinium p-toluenesulfonate; Wilkinson's catalyst; Grubbs catalyst first generation; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Luche reduction;
DOI:10.1016/j.tetlet.2005.07.152

Reference yield:

: 866430-81-1
[(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

: 883746-93-8
(4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-4H-7-oxa-benzocyclodecene-1,6-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

2: 83 percent / Ti(OiPr)4 / 10 h / 90 °C

3: 30 percent / Ti(OiPr)4 / (PCy₃)2(Cl)2Ru=CHPh / benzene / 2 h / 80 °C

4: 77 percent / H₂ / (Ph₃P)3RhCl / 45 h / 760 Torr

5: 81 percent / PPTS / ethanol / 12 h

6: 92 percent / PDC; 4 Angstroem MS / CH₂Cl₂ / 5 h

With 1H-imidazole; titanium(IV) isopropylate; dipyridinium dichromate; 4 Angstroem MS; hydrogen; pyridinium p-toluenesulfonate; Wilkinson's catalyst; Grubbs catalyst first generation; In ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.tetlet.2005.07.152