Technology Process of (2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-8,12-bis(4-methoxybenzyloxy)-6,10-dodecadiene
There total 20 articles about (2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-8,12-bis(4-methoxybenzyloxy)-6,10-dodecadiene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
sodium hexamethyldisilazane;
In
tetrahydrofuran;
at -78 - 0 ℃;
for 2h;
DOI:10.1021/jo8005599
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: DIBAlH / toluene / 0.33 h / -78 °C
2.1: imidazole / dimethylformamide / 0.5 h / 20 °C
3.1: NaBH4; CeCl3*7H2O / methanol / 0.25 h / -78 °C
4.1: Et3N / CH2Cl2 / 1 h / 0 °C
5.1: 91 percent / (DHQD)2PHAL; K2OsO2(OH)4; MeSO2NH2 / K3Fe(CN)6; K2CO3 / 2-methyl-propan-2-ol; H2O / 20 °C
6.1: p-TsOH*H2O / 0.33 h / 20 °C
7.1: Zn(NO3)2*6H2O / acetonitrile / 3 h / 50 °C
8.1: n-Bu2SnO / toluene / 12 h / Heating
8.2: 76 percent / n-Bu4NI / toluene / 1.5 h / Heating
9.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0.25 h / 20 °C
10.1: K2CO3 / methanol / 4 h / 20 °C
11.1: 95 percent / TPAP; NMO; MS 4 Angstroem / CH2Cl2 / 2 h / 20 °C
12.1: 14 percent / LiHMDS / tetrahydrofuran / 1 h / -78 - -20 °C
With
1H-imidazole; 2,6-dimethylpyridine; zinc(II) nitrate; sodium tetrahydroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; MS 4 Angstroem; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium hexamethyldisilazane;
potassium carbonate; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;
5.1: Sharpless asymmetric dihydroxylation / 12.1: Julia coupling reaction;
DOI:10.1016/j.tetlet.2007.03.152
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: imidazole / dimethylformamide / 0.5 h / 20 °C
2.1: NaBH4; CeCl3*7H2O / methanol / 0.25 h / -78 °C
3.1: Et3N / CH2Cl2 / 1 h / 0 °C
4.1: 91 percent / (DHQD)2PHAL; K2OsO2(OH)4; MeSO2NH2 / K3Fe(CN)6; K2CO3 / 2-methyl-propan-2-ol; H2O / 20 °C
5.1: p-TsOH*H2O / 0.33 h / 20 °C
6.1: Zn(NO3)2*6H2O / acetonitrile / 3 h / 50 °C
7.1: n-Bu2SnO / toluene / 12 h / Heating
7.2: 76 percent / n-Bu4NI / toluene / 1.5 h / Heating
8.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0.25 h / 20 °C
9.1: K2CO3 / methanol / 4 h / 20 °C
10.1: 95 percent / TPAP; NMO; MS 4 Angstroem / CH2Cl2 / 2 h / 20 °C
11.1: 14 percent / LiHMDS / tetrahydrofuran / 1 h / -78 - -20 °C
With
1H-imidazole; 2,6-dimethylpyridine; zinc(II) nitrate; sodium tetrahydroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; MS 4 Angstroem; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium hexamethyldisilazane;
potassium carbonate; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;
4.1: Sharpless asymmetric dihydroxylation / 11.1: Julia coupling reaction;
DOI:10.1016/j.tetlet.2007.03.152
