(1S,2S,4R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-ol

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Chemical Name:(1S,2S,4R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-ol
CAS No.:852546-57-7
Molecular Formula:C₃₃H₄₄O₅Si
Molecular Weight:548.795
Hs Code.:

Synonyms:(1S,2S,4R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-ol

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Chemical Property of (1S,2S,4R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-ol

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Technology Process of (1S,2S,4R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-ol

There total 17 articles about (1S,2S,4R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-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: 92.0%

: 852546-70-4
Thiocarbonic acid O-[(1S,2R,4S,5S,7R,8R)-5-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-hydroxy-7-(4-methoxy-benzyloxymethyl)-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-yl] ester O-p-tolyl ester

: 852546-57-7
(1S,2S,4R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-ol

Guidance literature:: at 180 ℃; for 2h;
DOI:10.1021/ol050339w

Reference yield: 61.0%

: C₁₀H₁₃LiSi

: 852546-56-6
(1S,4R,7R,8R)-8-(4-Methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-one

: C₂₃H₂₉⁽²⁾HO₅

: 852546-57-7
(1S,2S,4R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-ol

Guidance literature:: C₁₀H₁₃LiSi; (1S,4R,7R,8R)-8-(4-Methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-one; In tetrahydrofuran; at -50 - -20 ℃;

With water-d2; In tetrahydrofuran;
DOI:10.1021/ol050339w

Reference yield:

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

: 852546-57-7
(1S,2S,4R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-ol

Guidance literature:: Multi-step reaction with 14 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

12: 92 percent / TBAF / tetrahydrofuran / 3 h / Heating

13: 90 percent / pyridine / CH₂Cl₂ / 2 h / Heating

14: 92 percent / 2 h / 180 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; potassium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; 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