Technology Process of (3aS,5R,6R,9R,10S,14S,15R,15aR)-6-hydroxy-6,10,14-trimethyl-3-methylidene-2-oxohexadecahydro-5,9-epoxycyclotetradeca[b]furan-10,15-diyl diacetate
There total 21 articles about (3aS,5R,6R,9R,10S,14S,15R,15aR)-6-hydroxy-6,10,14-trimethyl-3-methylidene-2-oxohexadecahydro-5,9-epoxycyclotetradeca[b]furan-10,15-diyl diacetate 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:
- Guidance literature:
-
With
dmap; N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at 20 ℃;
for 1h;
Inert atmosphere;
DOI:10.1021/acs.orglett.5b00700
- Guidance literature:
-
Multi-step reaction with 13 steps
1: dihydrogen peroxide; ammonium molybdate(VI) tetrahydrate / water; ethanol / 0 - 20 °C
2: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere
3: acetic acid; water / tetrahydrofuran / 4 h / 20 °C
4: hydrogen; palladium 10% on activated carbon / ethyl acetate / 2 h / 20 °C / 760.05 Torr
5: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
6: tributylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere
7: carbon tetrabromide; triphenylphosphine; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
8: 2,3-dicyano-5,6-dichloro-p-benzoquinone / aq. buffer / 2 h / 20 °C / pH 7
9: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere
10: chromium dichloride / tetrahydrofuran / 16 h / 20 °C / Molecular sieve; Inert atmosphere
11: trifluoroacetic acid; methanol / dichloromethane / 1 h / 20 °C / Inert atmosphere
12: hydrogenchloride / methanol / 2 h / 20 °C / Inert atmosphere
13: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
With
chromium dichloride; hydrogenchloride; methanol; dmap; ammonium molybdate(VI) tetrahydrate; carbon tetrabromide; tributylphosphine; palladium 10% on activated carbon; water; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate;
2: |Julia-Kocienski Olefination / 6: |Morita-Baylis-Hillman Alkylation / 7: |Appel Halogenation / 10: |Nozaki-Hiyama-Kishi Reaction;
DOI:10.1021/acs.orglett.5b00700
- Guidance literature:
-
Multi-step reaction with 12 steps
1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere
2: acetic acid; water / tetrahydrofuran / 4 h / 20 °C
3: hydrogen; palladium 10% on activated carbon / ethyl acetate / 2 h / 20 °C / 760.05 Torr
4: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
5: tributylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere
6: carbon tetrabromide; triphenylphosphine; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
7: 2,3-dicyano-5,6-dichloro-p-benzoquinone / aq. buffer / 2 h / 20 °C / pH 7
8: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere
9: chromium dichloride / tetrahydrofuran / 16 h / 20 °C / Molecular sieve; Inert atmosphere
10: trifluoroacetic acid; methanol / dichloromethane / 1 h / 20 °C / Inert atmosphere
11: hydrogenchloride / methanol / 2 h / 20 °C / Inert atmosphere
12: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
With
chromium dichloride; hydrogenchloride; methanol; dmap; carbon tetrabromide; tributylphosphine; palladium 10% on activated carbon; water; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
1: |Julia-Kocienski Olefination / 5: |Morita-Baylis-Hillman Alkylation / 6: |Appel Halogenation / 9: |Nozaki-Hiyama-Kishi Reaction;
DOI:10.1021/acs.orglett.5b00700
