Technology Process of (3Z,16Z,22E)-(5S,6S,7R,11S,13S,14R,15S,18S,20S,21R)-14,18,20,24-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,16,22-tetraen-8-one
There total 31 articles about (3Z,16Z,22E)-(5S,6S,7R,11S,13S,14R,15S,18S,20S,21R)-14,18,20,24-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,16,22-tetraen-8-one 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:
-
-
887602-42-8
(3Z,16Z,22E)-(5S,6S,7R,11S,13S,14R,15S,18S,20S,21R)-14,18,20,24-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,16,22-tetraen-8-one
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: Ba(OH)2*8H2O / tetrahydrofuran / 2 h / 20 - 120 °C
1.2: 80 percent / tetrahydrofuran; H2O / 6 h
2.1: [Ph3P*CuH]6 / toluene / 8 h / 20 °C
With
barium dihydroxide; [Ph3P*CuH]6;
In
tetrahydrofuran; toluene;
DOI:10.1021/ja0609708
-
-
887602-42-8
(3Z,16Z,22E)-(5S,6S,7R,11S,13S,14R,15S,18S,20S,21R)-14,18,20,24-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,16,22-tetraen-8-one
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: 62 mg / Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
2.1: Ba(OH)2*8H2O / tetrahydrofuran / 2 h / 20 - 120 °C
2.2: 80 percent / tetrahydrofuran; H2O / 6 h
3.1: [Ph3P*CuH]6 / toluene / 8 h / 20 °C
With
barium dihydroxide; [Ph3P*CuH]6; Dess-Martin periodane;
In
tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja0609708
-
-
887602-42-8
(3Z,16Z,22E)-(5S,6S,7R,11S,13S,14R,15S,18S,20S,21R)-14,18,20,24-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,16,22-tetraen-8-one
- Guidance literature:
-
Multi-step reaction with 14 steps
1.1: 82 percent / CSA / CH2Cl2 / -10 - 20 °C
2.1: 65 percent / Ti(i-PrO)3Cl; i-PrMgCl / diethyl ether / 6 h
3.1: TBAF*H2O / dimethylformamide / 6 h / 75 °C
4.1: 0.131 g / i-Pr2NEt; DMAP / CH2Cl2 / 0 - 20 °C
5.1: Grubbs 2nd catalyst / toluene / 3 h / 60 °C
6.1: DIBAL-H / toluene / 0.25 h / -78 °C
7.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 0 °C
7.2: 0.098 g / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
8.1: 78 percent / DDQ; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 0 °C
9.1: DIBAL-H / CH2Cl2 / 3 h / 0 °C
10.1: Dess-Martin periodinane / CH2Cl2 / 0.75 h / 0 °C
11.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
11.2: tetrahydrofuran; hexane / 0.75 h / -78 - 0 °C
12.1: 62 mg / Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
13.1: Ba(OH)2*8H2O / tetrahydrofuran / 2 h / 20 - 120 °C
13.2: 80 percent / tetrahydrofuran; H2O / 6 h
14.1: [Ph3P*CuH]6 / toluene / 8 h / 20 °C
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triisopropoxytitanium(IV) chloride; dmap; barium dihydroxide; n-butyllithium; [Ph3P*CuH]6; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
7.2: Wittig olefination;
DOI:10.1021/ja0609708
