Technology Process of methyl (2Z,4E,6R,7S,8S,10E,14S)-14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-14-hydroxy-2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)tetradeca-2,4,10-trien-12-ynoate
There total 28 articles about methyl (2Z,4E,6R,7S,8S,10E,14S)-14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-14-hydroxy-2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)tetradeca-2,4,10-trien-12-ynoate 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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1132969-85-7
methyl (2Z,4E,6R,7S,8S,10E)-2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)trideca-2,4,10-trien-12-ynoate
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1132969-84-6
methyl (2Z,4E,6R,7S,8S,10E,14S)-14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-14-hydroxy-2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)tetradeca-2,4,10-trien-12-ynoate
- Guidance literature:
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methyl (2Z,4E,6R,7S,8S,10E)-2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)trideca-2,4,10-trien-12-ynoate;
With
(1S,2S)-N-Methylpseudoephedrine; zinc trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine;
In
toluene;
at 20 ℃;
for 0.583333h;
Inert atmosphere;
(4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde;
In
toluene;
at 20 ℃;
for 17h;
stereoselective reaction;
Inert atmosphere;
DOI:10.1002/anie.200804645
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(2Z,4E,6R,7S,8S,10E)-methyl 2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)trideca-2,4,10-trien-12-ynoate
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1132969-84-6
methyl (2Z,4E,6R,7S,8S,10E,14S)-14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-14-hydroxy-2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)tetradeca-2,4,10-trien-12-ynoate
- Guidance literature:
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(2Z,4E,6R,7S,8S,10E)-methyl 2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)trideca-2,4,10-trien-12-ynoate;
With
(-)-N-methylephedrine; zinc trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine;
In
toluene;
at 20 ℃;
for 35h;
Inert atmosphere;
(4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde;
In
toluene;
at 20 ℃;
for 17h;
Inert atmosphere;
DOI:10.1002/chem.201102797
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1132969-84-6
methyl (2Z,4E,6R,7S,8S,10E,14S)-14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-14-hydroxy-2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)tetradeca-2,4,10-trien-12-ynoate
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: lithium borohydride / tetrahydrofuran; diethyl ether; ethanol / 4.5 h / 0 - 20 °C / Inert atmosphere
2.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium bromide / dichloromethane / 0 °C / pH 8.6 / aq. buffer
2.2: 0.42 h / 0 °C
3.1: hydroxylamine hydrochloride / pyridine; ethanol / 12.5 h / 20 °C / Inert atmosphere
4.1: dichloromethane / -78 °C / Inert atmosphere
4.2: 0 - 20 °C / Inert atmosphere
5.1: toluene-4-sulfonic acid / methanol / 1.75 h / 20 °C / Inert atmosphere
6.1: pyridine / dichloromethane / 0.17 h / -78 - 0 °C / Inert atmosphere
7.1: hydrogen; boric acid / methanol; water / 3 h / 20 °C
8.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 118 h / -10 - -5 °C / Inert atmosphere
9.1: toluene-4-sulfonic acid / 0.33 h / 20 °C / Inert atmosphere
10.1: lithium hydroxide / tetrahydrofuran; methanol; water / 0.42 h / 20 °C
11.1: sodium periodate / chloroform / 0.47 h / 20 °C / Inert atmosphere
12.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / toluene / 35 h / 20 °C / Inert atmosphere
12.2: 17 h / 20 °C / Inert atmosphere
With
pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium periodate; lithium borohydride; (-)-N-methylephedrine; hydroxylamine hydrochloride; hydrogen; boric acid; zinc trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; potassium bromide; lithium hydroxide; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; toluene; acetonitrile;
DOI:10.1002/chem.201102797
