(1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol

Base Information

Chemical Name:(1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol
CAS No.:852546-60-2
Molecular Formula:C₃₉H₆₀O₆Si₂
Molecular Weight:681.073
Hs Code.:

(1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol

Synonyms:(1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol

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Chemical Property of (1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol

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Technology Process of (1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol

There total 14 articles about (1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol 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: 89.0%

: 852546-59-9
(1S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-one

: 103731-34-6,103731-35-7,1146976-17-1
(E)-1-(tri-n-butylstannyl)-2-(dimethylphenylsilyl)ethene

: 852546-60-2
(1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 3h;
DOI:10.1021/ol050339w

Reference yield:

: Acetic acid (1S,4R)-2,3-dibromo-4-hydroxy-cyclohexyl ester

: 852546-60-2
(1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol

Guidance literature:: Multi-step reaction with 11 steps

1: Zn / ethanol / Heating

2: imidazole / CH₂Cl₂ / 25 °C

3: K₂CO₃ / methanol / 25 °C

4: 98 percent / CrO₃; pyridine / CH₂Cl₂ / 25 °C

5: 42 percent / diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 16 h / -78 - 0 °C

6: 86 percent / DIBAL / tetrahydrofuran; hexane / 7.5 h / -78 - 25 °C

7: 96 percent / pyridine / 8 h / -15 - 25 °C

8: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

9: 94 percent / K₂CO₃ / methanol / 24 h / Heating

10: 91 percent / aq. KOH; (n-Bu)4NI / CH₂Cl₂ / 4 h / Heating

11: 89 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - -20 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; potassium hydroxide; n-butyllithium; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; diisopropylamine; zinc; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 8: Dess-Martin oxidation;
DOI:10.1021/ol050339w

Reference yield:

: 852546-68-0
(1S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-one

: 852546-60-2
(1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / aq. KOH; (n-Bu)4NI / CH₂Cl₂ / 4 h / Heating

2: 89 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - -20 °C

With potassium hydroxide; n-butyllithium; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol050339w