Technology Process of 1,5-Dodecadien-4-ol,
12-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-3,8,9-trimethoxy-5,7,11-trimeth
yl-, (3S,4S,5E,7S,8R,9S,11S)-
There total 15 articles about 1,5-Dodecadien-4-ol,
12-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-3,8,9-trimethoxy-5,7,11-trimeth
yl-, (3S,4S,5E,7S,8R,9S,11S)- 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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922166-93-6
(E)-(3S,4S,7S,8R,9S,11S)-12-tert-butyldiphenylsilyloxy-3,8,9-trimethoxy-5,7,11-trimethyldodec-1,5-dien-4-ol
- Guidance literature:
-
(E)-(4S,5R,6S,8S)-9-tert-butyldiphenylsilyloxy-5,6-dimethoxy-2,4,8-trimethylnon-2-enal; <(Z)-γ-methoxyallyl>diisocampheylborane;
With
boron trifluoride diethyl etherate;
In
tetrahydrofuran; cyclohexane;
at -78 - -5 ℃;
With
ethanolamine;
In
pentane;
at 0 ℃;
for 2.5h;
DOI:10.1021/ol062642i
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-
922166-93-6
(E)-(3S,4S,7S,8R,9S,11S)-12-tert-butyldiphenylsilyloxy-3,8,9-trimethoxy-5,7,11-trimethyldodec-1,5-dien-4-ol
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 4.37 mg / aq. HCl / tetrahydrofuran; CH2Cl2 / 3 h / 20 °C
2.1: 96 percent / (S,S)-chiral titanium complex / diethyl ether; tetrahydrofuran / 5 h / -78 °C
3.1: 97 percent / KH / tetrahydrofuran / 0 - 20 °C
4.1: 98 percent / [1,3-Mes2-(N2C3H5)]Cl2(PCy3)Ru=CHPh; N-allyl-N-tritylamine; diisopropylethylamine / toluene / 3.5 h / Heating
5.1: OsO4; H2O; N-methylmorpholine N-oxide / acetone / 16 h / 20 °C
6.1: aq. NaIO4 / acetone / 2.5 h / 20 °C
7.1: 2.73 g / 4 Angstroem molecular sieves / toluene / 2.5 h / -78 - 0 °C
8.1: 92 percent / KH / tetrahydrofuran / 0 - 20 °C
9.1: OsO4; H2O; N-methylmorpholine N-oxide / acetone / 18 h / 20 °C
10.1: aq. NaIO4 / acetone / 2.5 h / 20 °C
11.1: s-BuLi / tetrahydrofuran; cyclohexane / 4.5 h / -78 - -20 °C
11.2: 1.18 g / citric acid / tetrahydrofuran; cyclohexane; H2O / pH 4 - 5
12.1: BF3*Et2O / tetrahydrofuran; cyclohexane / -78 - -5 °C
12.2: 1.49 g / ethanolamine / pentane / 2.5 h / 0 °C
With
hydrogenchloride; sodium periodate; osmium(VIII) oxide; (S,S)-chiral titanium; [1,3-Mes2-(N2C3H5)]Cl2(PCy3)Ru=CHPh; 4 A molecular sieve; boron trifluoride diethyl etherate; N-tritylprop-2-en-1-amine; water; sec.-butyllithium; potassium hydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; acetone; toluene;
11.1: Corey-Schlessinger olefination;
DOI:10.1021/ol062642i
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-
922166-93-6
(E)-(3S,4S,7S,8R,9S,11S)-12-tert-butyldiphenylsilyloxy-3,8,9-trimethoxy-5,7,11-trimethyldodec-1,5-dien-4-ol
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: OsO4; H2O; N-methylmorpholine N-oxide / acetone / 16 h / 20 °C
2.1: aq. NaIO4 / acetone / 2.5 h / 20 °C
3.1: 2.73 g / 4 Angstroem molecular sieves / toluene / 2.5 h / -78 - 0 °C
4.1: 92 percent / KH / tetrahydrofuran / 0 - 20 °C
5.1: OsO4; H2O; N-methylmorpholine N-oxide / acetone / 18 h / 20 °C
6.1: aq. NaIO4 / acetone / 2.5 h / 20 °C
7.1: s-BuLi / tetrahydrofuran; cyclohexane / 4.5 h / -78 - -20 °C
7.2: 1.18 g / citric acid / tetrahydrofuran; cyclohexane; H2O / pH 4 - 5
8.1: BF3*Et2O / tetrahydrofuran; cyclohexane / -78 - -5 °C
8.2: 1.49 g / ethanolamine / pentane / 2.5 h / 0 °C
With
sodium periodate; osmium(VIII) oxide; 4 A molecular sieve; boron trifluoride diethyl etherate; water; sec.-butyllithium; potassium hydride; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; cyclohexane; acetone; toluene;
7.1: Corey-Schlessinger olefination;
DOI:10.1021/ol062642i
