Technology Process of (2S,3S,4R)-2,3-epoxy-4-(tert-butyldimethylsiloxy)-2-methyl-5-(triisopropylsiloxy)-pent-1-ol
There total 1 articles about (2S,3S,4R)-2,3-epoxy-4-(tert-butyldimethylsiloxy)-2-methyl-5-(triisopropylsiloxy)-pent-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 4 steps
1: 90 percent / DIBAL / -78 °C
2: 80 percent / (+)-DIPT; Ti(O-i-Pr)4; TBHP / MS 4 Angstroem / CH2Cl2 / 6 h / -20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride;
MS 4 Angstroem;
In
dichloromethane;
4: Sharpless asymmetric epoxidation;
DOI:10.1021/ja034332q
- Guidance literature:
-
Multi-step reaction with 11 steps
1: TPAP; NMO; MS 4 Angstroem / CH2Cl2 / 0.5 h / 20 °C
2: 837 mg / tetrahydrofuran / 0.5 h / -20 °C
3: 99 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -20 °C
4: 93 percent / TiCl4 / CH2Cl2 / 0.33 h / -78 °C
5: 82 percent / HCl; ethylene glycol / diethyl ether; tetrahydrofuran
6: 82 percent / KH / tetrahydrofuran / 2 h / Heating
7: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
8: 84 percent / HCl / diethyl ether / 2 h / 20 °C
9: 98 percent / DMAP; imidazole / CH2Cl2 / 20 °C
10: 85 percent / NMO; aq. OsO4 / acetone / 4 h / 20 °C
11: DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 0 °C
With
1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; MS 4 Angstroem; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium hydride; ethylene glycol; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone;
4: Tsuchihashi-Suzuki rearrangement / 11: Swern oxidation;
DOI:10.1021/ja034332q
- Guidance literature:
-
Multi-step reaction with 6 steps
1: TPAP; NMO; MS 4 Angstroem / CH2Cl2 / 0.5 h / 20 °C
2: 837 mg / tetrahydrofuran / 0.5 h / -20 °C
3: 99 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -20 °C
4: 93 percent / TiCl4 / CH2Cl2 / 0.33 h / -78 °C
5: 82 percent / HCl; ethylene glycol / diethyl ether; tetrahydrofuran
6: 82 percent / KH / tetrahydrofuran / 2 h / Heating
With
2,6-dimethylpyridine; hydrogenchloride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; MS 4 Angstroem; titanium tetrachloride; potassium hydride; ethylene glycol;
In
tetrahydrofuran; diethyl ether; dichloromethane;
4: Tsuchihashi-Suzuki rearrangement;
DOI:10.1021/ja034332q
