Technology Process of (2S,3R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-8,10,16-trimethyl-19-(trityloxy)nonadeca-11,17-dien-3-ol
There total 19 articles about (2S,3R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-8,10,16-trimethyl-19-(trityloxy)nonadeca-11,17-dien-3-ol 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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861822-09-5
(2R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-8,10,16-trimethyl-19-(trityloxy)nonadeca-11,17-dien-3-one
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861822-02-8
(2S,3R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-8,10,16-trimethyl-19-(trityloxy)nonadeca-11,17-dien-3-ol
- Guidance literature:
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With
lithium tri-t-butoxyaluminum hydride;
In
tetrahydrofuran;
DOI:10.1021/ol050808u
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861822-02-8
(2S,3R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-8,10,16-trimethyl-19-(trityloxy)nonadeca-11,17-dien-3-ol
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: 86 percent / n-butyllithium
2.1: 95 percent / (S,S)-Noyori catalyst / propan-2-ol
3.1: 100 percent / H2 / Lindlar catalyst / toluene
4.1: 96 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
5.1: 71 percent / HF*pyridine; pyridine / tetrahydrofuran / 21 h / 0 °C
6.1: Dess-Martin periodinane / CH2Cl2 / 1 h
7.1: Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C
7.2: 1.22 g / tetrahydrofuran; H2O / 12 h
8.1: 65 percent / NaBH4 / NiCl2 / methanol; tetrahydrofuran; H2O / 1 h / 0 °C
9.1: 95 percent / Li(t-BuO)3AlH / tetrahydrofuran / 30 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; barium dihydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; lithium tri-t-butoxyaluminum hydride;
Lindlar's catalyst; (S,S)-Noyori catalyst; nickel dichloride;
In
tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; toluene;
3.1: Lindlar hydrogenation / 6.1: Dess-Martin oxidation / 7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jm061385k
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861822-02-8
(2S,3R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-8,10,16-trimethyl-19-(trityloxy)nonadeca-11,17-dien-3-ol
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: n-butyllithium
2.1: 86 percent / n-butyllithium
3.1: 95 percent / (S,S)-Noyori catalyst / propan-2-ol
4.1: 100 percent / H2 / Lindlar catalyst / toluene
5.1: 96 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
6.1: 71 percent / HF*pyridine; pyridine / tetrahydrofuran / 21 h / 0 °C
7.1: Dess-Martin periodinane / CH2Cl2 / 1 h
8.1: Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C
8.2: 1.22 g / tetrahydrofuran; H2O / 12 h
9.1: 65 percent / NaBH4 / NiCl2 / methanol; tetrahydrofuran; H2O / 1 h / 0 °C
10.1: 95 percent / Li(t-BuO)3AlH / tetrahydrofuran / 30 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; barium dihydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; lithium tri-t-butoxyaluminum hydride;
Lindlar's catalyst; (S,S)-Noyori catalyst; nickel dichloride;
In
tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; toluene;
4.1: Lindlar hydrogenation / 7.1: Dess-Martin oxidation / 8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jm061385k