(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

Base Information

Chemical Name:(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
CAS No.:852546-59-9
Molecular Formula:C₂₉H₄₆O₆Si
Molecular Weight:518.766
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 13 articles about (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 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: 91.0%

: 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

: 824-94-2
p-methoxybenzyl chloride

: 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

Guidance literature:: With potassium hydroxide; tetra-(n-butyl)ammonium iodide; In dichloromethane; for 4h; Heating;
DOI:10.1021/ol050339w

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 10 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

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:

: 852546-52-2
(1S,2R,3S,4S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-5-oxo-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

: 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

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / DIBAL / tetrahydrofuran; hexane / 7.5 h / -78 - 25 °C

2: 96 percent / pyridine / 8 h / -15 - 25 °C

3: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

4: 94 percent / K₂CO₃ / methanol / 24 h / Heating

5: 91 percent / aq. KOH; (n-Bu)4NI / CH₂Cl₂ / 4 h / Heating

With pyridine; potassium hydroxide; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; hexane; dichloromethane; 3: Dess-Martin oxidation;
DOI:10.1021/ol050339w