Technology Process of 7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile
There total 20 articles about 7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile 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:
- Guidance literature:
-
With
methanesulfonamide; AD-mix-β*;
In
water; tert-butyl alcohol;
for 16h;
Optical yield = 13.043 %de; regioselective reaction;
DOI:10.1021/jo3026077
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 65 percent / TiCl4 / CH2Cl2 / 0.25 h / -78 °C
2.1: SOCl2; pyridine / toluene / 0.5 h / -78 °C
2.2: TBAF / tetrahydrofuran / 0 - 20 °C
3.1: 81 percent / PPh3; DEAD / diethyl ether; toluene / 0 - 20 °C
4.1: 77 percent / Et3N / CH2Cl2 / -78 - 20 °C
5.1: MeSO2NH2; (DHQD)2PHAL; K2OsO4*2H2O / K2CO3; K3Fe(CN)6 / H2O; 2-methyl-propan-2-ol / 16 h
With
pyridine; potassium osmate(VI); thionyl chloride; methanesulfonamide; titanium tetrachloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; diethylazodicarboxylate;
potassium carbonate; potassium hexacyanoferrate(III);
In
diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol;
3.1: Mitsunobu reaction / 5.1: Sharpless dihydroxylation;
DOI:10.1021/ol051544e
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 99 percent / LiBH4 / methanol; tetrahydrofuran / 0 - 20 °C
2.1: 99 percent / Et3N / CH2Cl2 / -78 - 20 °C
3.1: 65 percent / TiCl4 / CH2Cl2 / 0.25 h / -78 °C
4.1: SOCl2; pyridine / toluene / 0.5 h / -78 °C
4.2: TBAF / tetrahydrofuran / 0 - 20 °C
5.1: 81 percent / PPh3; DEAD / diethyl ether; toluene / 0 - 20 °C
6.1: 77 percent / Et3N / CH2Cl2 / -78 - 20 °C
7.1: MeSO2NH2; (DHQD)2PHAL; K2OsO4*2H2O / K2CO3; K3Fe(CN)6 / H2O; 2-methyl-propan-2-ol / 16 h
With
pyridine; potassium osmate(VI); lithium borohydride; thionyl chloride; methanesulfonamide; titanium tetrachloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; diethylazodicarboxylate;
potassium carbonate; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol;
5.1: Mitsunobu reaction / 7.1: Sharpless dihydroxylation;
DOI:10.1021/ol051544e
