(1R,2R)-1-[(1S,2R,3R,4R,7S)-7-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-7-hydroxy-3-(4-methoxy-benzyloxymethyl)-bicyclo[2.2.2]oct-5-en-2-yl]-propane-1,2-diol

Base Information

Chemical Name:(1R,2R)-1-[(1S,2R,3R,4R,7S)-7-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-7-hydroxy-3-(4-methoxy-benzyloxymethyl)-bicyclo[2.2.2]oct-5-en-2-yl]-propane-1,2-diol
CAS No.:852546-71-5
Molecular Formula:C₃₀H₄₀O₅Si
Molecular Weight:508.73
Hs Code.:

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

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

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

There total 16 articles about (1R,2R)-1-[(1S,2R,3R,4R,7S)-7-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-7-hydroxy-3-(4-methoxy-benzyloxymethyl)-bicyclo[2.2.2]oct-5-en-2-yl]-propane-1,2-diol 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: 88.0%

: 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

: 852546-71-5
(1R,2R)-1-[(1S,2R,3R,4R,7S)-7-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-7-hydroxy-3-(4-methoxy-benzyloxymethyl)-bicyclo[2.2.2]oct-5-en-2-yl]-propane-1,2-diol

Guidance literature:: With camphor-10-sulfonic acid; water; In methanol; at 20 ℃; for 24h;
DOI:10.1021/ol050339w

Reference yield:

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

: 852546-71-5
(1R,2R)-1-[(1S,2R,3R,4R,7S)-7-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-7-hydroxy-3-(4-methoxy-benzyloxymethyl)-bicyclo[2.2.2]oct-5-en-2-yl]-propane-1,2-diol

Guidance literature:: Multi-step reaction with 15 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

15: 88 percent / CSA; H₂O / methanol / 24 h / 20 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; potassium hydroxide; n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; 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

: 852546-71-5
(1R,2R)-1-[(1S,2R,3R,4R,7S)-7-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-7-hydroxy-3-(4-methoxy-benzyloxymethyl)-bicyclo[2.2.2]oct-5-en-2-yl]-propane-1,2-diol

Guidance literature:: Multi-step reaction with 6 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

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

4: 90 percent / pyridine / CH₂Cl₂ / 2 h / Heating

5: 92 percent / 2 h / 180 °C

6: 88 percent / CSA; H₂O / methanol / 24 h / 20 °C

With pyridine; potassium hydroxide; n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ol050339w