Technology Process of (2Z,4E,6R,7S,9S,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-1,7,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol
There total 31 articles about (2Z,4E,6R,7S,9S,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-1,7,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-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:
-
-
945402-12-0
1-(((3Z,5S,6S,7R,8R,11Z,13S,14R,15S,16Z)-8,14-bis(tert-butyldimethylsilyloxy)-17-iodo-5,7,13,15-tetramethylheptadeca-1,3,11,16-tetraen-6-yloxy)methyl)-4-methoxybenzene
-
-
945402-13-1
(2Z,4E,6R,7S,9S,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-1,7,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol
-
-
945402-21-1
(2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-1,7,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol
- Guidance literature:
-
1-(((3Z,5S,6S,7R,8R,11Z,13S,14R,15S,16Z)-8,14-bis(tert-butyldimethylsilyloxy)-17-iodo-5,7,13,15-tetramethylheptadeca-1,3,11,16-tetraen-6-yloxy)methyl)-4-methoxybenzene;
With
tert.-butyl lithium;
In
diethyl ether; pentane;
at -78 ℃;
for 0.333333h;
C22H44O3Si2;
In
diethyl ether; pentane;
at -78 - -10 ℃;
for 1.16667h;
Further stages.;
DOI:10.1021/jm061385k
-
-
945402-13-1
(2Z,4E,6R,7S,9S,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-1,7,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 91 percent / Grubbs second generation catalyst / CH2Cl2 / 15 h
2.1: 18-crown-6; potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1.2 h / -78 - -45 °C
2.2: 100 percent / tetrahydrofuran; toluene / 6 h / -78 - 20 °C
3.1: 92 percent / HF*pyridine / tetrahydrofuran / 0 - 20 °C
4.1: triethylamine; SO3*pyridine / CH2Cl2; dimethylsulfoxide / 1.03 h / 0 °C
5.1: NaH2PO4*H2O; 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 2.25 h / 0 - 20 °C
6.1: 0.36 g / triethylamine; DCC / CH2Cl2 / 0 - 20 °C
7.1: DIBALH / tetrahydrofuran; hexane / 1 h / -78 - 20 °C
8.1: 0.38 g / 2,6-lutidine / CH2Cl2 / 1 h / -78 °C
9.1: tert-butyllithium / diethyl ether; pentane / 0.33 h / -78 °C
9.2: 27 percent / diethyl ether; pentane / 1.17 h / -78 - -10 °C
With
2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 18-crown-6 ether; pyridine-SO3 complex; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; dicyclohexyl-carbodiimide;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; pentane;
1.1: Grubbs-II cross-metathesis / 2.2: Still-Gennari olefination;
DOI:10.1021/jm061385k
-
-
945402-13-1
(2Z,4E,6R,7S,9S,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-1,7,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: Et2BOMe / tetrahydrofuran; methanol / 0.67 h / -78 °C
1.2: 85 percent / NaBH4 / tetrahydrofuran; methanol / 7.17 h / -78 °C
2.1: 60 percent / DDQ; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 0 - 20 °C
3.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / -78 - 0 °C
4.1: 41 percent / DIBALH / CH2Cl2; hexane / 12.5 h / -78 - -45 °C
5.1: triethylamine; SO3*pyridine / CH2Cl2; dimethylsulfoxide / 1.17 h / 0 °C
6.1: CrCl2 / tetrahydrofuran / 17 h / 20 °C
7.1: 1.85 g / NaH / tetrahydrofuran / 1.3 h / 0 - 20 °C
8.1: 75 percent / HF*pyridine; pyridine / tetrahydrofuran / 6 h / 0 - 20 °C
9.1: 93 percent / triphenylphosphine; imidazole; I2 / benzene; diethyl ether / 0.67 h / 20 °C
10.1: 78 percent / triphenylphosphine / benzene / 16 h / 20 - 80 °C
11.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C
11.2: 82 percent / tetrahydrofuran / -78 - 20 °C
12.1: tert-butyllithium / diethyl ether; pentane / 0.33 h / -78 °C
12.2: 27 percent / diethyl ether; pentane / 1.17 h / -78 - -10 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; pyridine-SO3 complex; 4 A molecular sieve; diethyl methoxy borane; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; pentane; benzene;
6.1: Nozaki-Hiyama-Kishi reaction / 7.1: Peterson elimination;
DOI:10.1021/jm061385k
