Technology Process of (2S,3S,4R,6R)-6-(6-ethyl-3,5-dimethyl-4-oxo-4H-2-pyranyl)-3-(4-methoxybenzyloxy)-2,4-dimethyl5-oxoheptanoic acid
There total 9 articles about (2S,3S,4R,6R)-6-(6-ethyl-3,5-dimethyl-4-oxo-4H-2-pyranyl)-3-(4-methoxybenzyloxy)-2,4-dimethyl5-oxoheptanoic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
2-((2S,3S,4S,5R,6R)-3,7-dihydroxy-5-((4-methoxybenzyl)oxy)-4,6-dimethylheptan-2-yl)-6-ethyl-3,5-dimethyl-4H-pyran-4-one;
With
dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -78 - -30 ℃;
for 1h;
With
sodium chlorite; disodium hydrogenphosphate; 2-methyl-but-2-ene;
In
tert-butyl alcohol;
at 20 ℃;
for 1h;
Further stages.;
DOI:10.1021/ol000027n
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 94 percent / TfOH / diethyl ether
2.1: 87 percent / TBAF / tetrahydrofuran
3.1: 97 percent / K2CO3 / methanol / 60 °C
4.1: DMSO; COCl2; Et3N / CH2Cl2 / 1 h / -78 - -30 °C
4.2: 96 percent / aq. NaClO2; aq. Na2HPO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C
With
tetrabutyl ammonium fluoride; potassium carbonate; dimethyl sulfoxide; triethylamine;
trifluorormethanesulfonic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane;
1.1: Etherification / 2.1: desilylation / 3.1: Deacetylation / 4.1: Swern oxidation / 4.2: Oxidation;
DOI:10.1021/ol000027n
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: Sn(OTf)2; Et3N / CH2Cl2 / 3 h / -78 °C
1.2: 74 percent / CH2Cl2 / 1.5 h / -78 °C
2.1: 100 percent / SmI2 / tetrahydrofuran / 16 h / -26 °C
3.1: 94 percent / TfOH / diethyl ether
4.1: 87 percent / TBAF / tetrahydrofuran
5.1: 97 percent / K2CO3 / methanol / 60 °C
6.1: DMSO; COCl2; Et3N / CH2Cl2 / 1 h / -78 - -30 °C
6.2: 96 percent / aq. NaClO2; aq. Na2HPO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C
With
tin(II) trifluoromethanesulfonate; samarium diiodide; tetrabutyl ammonium fluoride; potassium carbonate; dimethyl sulfoxide; triethylamine;
trifluorormethanesulfonic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane;
1.1: enolization / 1.2: Addition / 2.1: Acetylation / 3.1: Etherification / 4.1: desilylation / 5.1: Deacetylation / 6.1: Swern oxidation / 6.2: Oxidation;
DOI:10.1021/ol000027n
