Technology Process of (1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4-[hydroxy(phenyl)methyl]-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-one
There total 15 articles about (1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4-[hydroxy(phenyl)methyl]-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-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:
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![(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.0<sup>2,7</sup>.0<sup>2,10</sup>]undecan-3-one](/Databaselist/images/loading.webp)
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878633-41-1
(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-one
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313548-01-5
(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4-[hydroxy(phenyl)methyl]-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-one
- Guidance literature:
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(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-one;
With
lithium hexamethyldisilazane;
In
tetrahydrofuran;
at -78 ℃;
for 0.5h;
benzaldehyde;
In
tetrahydrofuran;
at -78 ℃;
for 1h;
DOI:10.1016/j.tet.2005.10.082
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350482-06-3
(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-2-bromo-3,5-epoxy-6,7-(O-isopropylidenedioxy)perhydro-endo-1,4-methanonaphthalen-8-one
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313548-01-5
(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4-[hydroxy(phenyl)methyl]-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-one
- Guidance literature:
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(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-2-bromo-3,5-epoxy-6,7-(O-isopropylidenedioxy)perhydro-endo-1,4-methanonaphthalen-8-one;
With
lithium hexamethyldisilazane;
In
tetrahydrofuran;
at -78 ℃;
for 0.5h;
benzaldehyde;
In
tetrahydrofuran;
at -78 ℃;
for 1h;
DOI:10.1016/j.tet.2005.10.082
-
-
313548-01-5
(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4-[hydroxy(phenyl)methyl]-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-one
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: 53 percent / sodium borohydride / H2O; tetrahydrofuran / 1 h / 20 °C
2.1: 98 percent / diethyl azodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 3 h / 20 °C
3.1: 100 percent / potassium hydroxide / methanol / 3 h / 20 °C
4.1: 67 percent / diethyl azodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 3 h / 20 °C
5.1: 92 percent / 3-chloroperoxybenzoic acid; sodium hydrogen carbonate / CH2Cl2 / 24 h / 20 °C
6.1: soduim borohydride; diphenyl diselenide / ethanol / 1 h / Heating
6.2: 78 percent / hydrogen peroxide / H2O; ethanol / 1 h / Heating
7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
8.1: 97 percent / diethylaluminium chloride / hexane; CH2Cl2 / 2 h / -78 - 0 °C
9.1: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
10.1: 86 percent / N-bromosuccinimide / CH2Cl2 / 1 h / 20 °C
11.1: 98 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C
12.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C
12.2: tetrahydrofuran / 1 h / -78 °C
With
potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; diphenyl diselenide; tetrabutyl ammonium fluoride; diethylaluminium chloride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; toluene;
2.1: Mitsunobu reaction / 7.1: Dess-Martin oxidation / 8.1: Diels-Alder reaction;
DOI:10.1016/j.tet.2005.10.082
