Technology Process of (E)-(2S,3S,5S,6R,7R)-7-(tert-butyldiphenylsilanoxy)-2,3-epoxy-5-(4-methoxybenzyloxy)-6-methyldeca-8-en-1-ol
There total 12 articles about (E)-(2S,3S,5S,6R,7R)-7-(tert-butyldiphenylsilanoxy)-2,3-epoxy-5-(4-methoxybenzyloxy)-6-methyldeca-8-en-1-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:
- Guidance literature:
-
(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dien-1-ol;
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate;
In
dichloromethane;
for 0.666667h;
Further stages.;
DOI:10.1021/ol015753k
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 67 percent / CSA / CH2Cl2 / 40 h
2: 74 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 20 h
3: 100 percent / NaIO4 / H2O; tetrahydrofuran / 0.5 h
4: 88 percent / CH2Cl2 / 1.5 h
5: 96 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C
6: 95 percent / TBHP; Ti(OiPr)4; diethyl-L-tartrate / CH2Cl2 / 0.67 h
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; AD-mix-α; diethyl (2R,3R)-tartrate; camphor-10-sulfonic acid; diisobutylaluminium hydride;
In
tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
4: Wittig olefination;
DOI:10.1021/ol015753k
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 99 percent / imidazole / CH2Cl2 / 20 h
2: 86 percent / LiBH4 / diethyl ether; H2O / -20 - 5 °C
3: 98 percent / dimethylsulfoxide; oxalyl chloride; triethylamine / CH2Cl2 / -78 - -30 °C
4: 85 percent / diethyl ether / 3 h / -78 °C
5: 67 percent / CSA / CH2Cl2 / 40 h
6: 74 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 20 h
7: 100 percent / NaIO4 / H2O; tetrahydrofuran / 0.5 h
8: 88 percent / CH2Cl2 / 1.5 h
9: 96 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C
10: 95 percent / TBHP; Ti(OiPr)4; diethyl-L-tartrate / CH2Cl2 / 0.67 h
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; AD-mix-α; lithium borohydride; oxalyl dichloride; diethyl (2R,3R)-tartrate; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol;
3: Swern oxidation / 8: Wittig olefination;
DOI:10.1021/ol015753k
