2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester
CAS No.:852546-66-8
Molecular Formula:C₂₈H₃₈O₇S
Molecular Weight:518.672
Hs Code.:

2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester

Synonyms:2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester

There total 12 articles about 2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester 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: 90.0%

: 852546-65-7
2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-7-hydroxy-5-oxo-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester

: 937-63-3
p-Tolyl chlorothionoformate

: 852546-66-8
2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester

Guidance literature:: With pyridine; In dichloromethane; at 25 ℃; for 6h;
DOI:10.1021/ol050339w

Reference yield:

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

: 852546-66-8
2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester

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: 96 percent / TBAF / tetrahydrofuran / 3 h / 25 °C

10: 90 percent / pyridine / CH₂Cl₂ / 6 h / 25 °C

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

: 852546-66-8
2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester

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: 96 percent / TBAF / tetrahydrofuran / 3 h / 25 °C

5: 90 percent / pyridine / CH₂Cl₂ / 6 h / 25 °C

With pyridine; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; 3: Dess-Martin oxidation;
DOI:10.1021/ol050339w