Technology Process of (E)-(R)-4-{(3aR,4R,7S,7aR)-2,2-Dimethyl-7-[2-(1-phenyl-1H-tetrazole-5-sulfonyl)-ethyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl}-3-methyl-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester
There total 10 articles about (E)-(R)-4-{(3aR,4R,7S,7aR)-2,2-Dimethyl-7-[2-(1-phenyl-1H-tetrazole-5-sulfonyl)-ethyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl}-3-methyl-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
magnesium sulfate; toluene-4-sulfonic acid;
In
ethyl acetate;
for 1h;
DOI:10.1021/ja042827p
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 76 percent / 48 h / 110 °C
2.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C
3.1: OsO4; potassium ferricyanide; (DHDQ)2PHAL / K2CO3; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 2 h / 0 °C
3.2: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
4.1: 8.98 g / NaBH4 / ethanol / 0.5 h
5.1: 85 percent / TiCl4; Et3SiH / CH2Cl2 / 2.5 h / -50 °C
6.1: PPh3; DIAD / tetrahydrofuran / 4 h / 20 °C
7.1: 7.65 g / aq. H2O2; ammonium molybdate tetrahydrate / ethanol / 20 °C
8.1: 87 percent / OsO4; N-methylmorpholine N-oxide monohydrate / acetone; H2O; 2-methyl-propan-2-ol / 20 °C
9.1: 98 percent / p-TsOH; MgSO4 / ethyl acetate / 1 h
With
2,6-dimethylpyridine; triethylsilane; sodium tetrahydroborate; osmium(VIII) oxide; ammonium molybdate(VI) tetrahydrate; di-isopropyl azodicarboxylate; dihydrogen peroxide; titanium tetrachloride; magnesium sulfate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; potassium hexacyanoferrate(III);
methanesulfonamide; potassium carbonate;
In
tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; acetone; tert-butyl alcohol;
DOI:10.1021/ja042827p
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 76 percent / 48 h / 110 °C
2.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C
3.1: OsO4; potassium ferricyanide; (DHDQ)2PHAL / K2CO3; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 2 h / 0 °C
3.2: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
4.1: 8.98 g / NaBH4 / ethanol / 0.5 h
5.1: 85 percent / TiCl4; Et3SiH / CH2Cl2 / 2.5 h / -50 °C
6.1: PPh3; DIAD / tetrahydrofuran / 4 h / 20 °C
7.1: 7.65 g / aq. H2O2; ammonium molybdate tetrahydrate / ethanol / 20 °C
8.1: 87 percent / OsO4; N-methylmorpholine N-oxide monohydrate / acetone; H2O; 2-methyl-propan-2-ol / 20 °C
9.1: 98 percent / p-TsOH; MgSO4 / ethyl acetate / 1 h
With
2,6-dimethylpyridine; triethylsilane; sodium tetrahydroborate; osmium(VIII) oxide; ammonium molybdate(VI) tetrahydrate; di-isopropyl azodicarboxylate; dihydrogen peroxide; titanium tetrachloride; magnesium sulfate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; potassium hexacyanoferrate(III);
methanesulfonamide; potassium carbonate;
In
tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; acetone; tert-butyl alcohol;
DOI:10.1021/ja042827p
