Technology Process of (3S,3aS,5R,6R,7R,7aS)-3,6-Dihydroxy-7-methoxy-5-methyl-3-phenyl-hexahydro-furo[3,2-b]pyran-2-one
There total 11 articles about (3S,3aS,5R,6R,7R,7aS)-3,6-Dihydroxy-7-methoxy-5-methyl-3-phenyl-hexahydro-furo[3,2-b]pyran-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(3S,3aS,5R,6S,7R,7aS)-3,6,7-Trihydroxy-5-methyl-3-phenyl-hexahydro-furo[3,2-b]pyran-2-one;
With
di(n-butyl)tin oxide;
In
toluene;
for 6h;
Heating;
methyl iodide;
With
cesium fluoride;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 48h;
DOI:10.1021/ol050975u
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 66 percent / CsF / Pd(PPh3)4; CuI / dimethylformamide / 24 h / 45 °C
2.1: 49 percent / AD-mix α / 2-methyl-propan-2-ol; H2O / 24 h / 20 °C
3.1: BH3*THF / tetrahydrofuran / 27 h / 0 - 20 °C
3.2: 75 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0 - 20 °C
4.1: 93 percent / imidazole / dimethylformamide / 24 h / 20 °C
5.1: 72 percent / MeOH; 10-camphorsulfonic acid / CH2Cl2 / 5 h / 0 °C
6.1: 99 percent / SO3*pyridine; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C
7.1: 92 percent / I2; KOH / 0 - 20 °C
8.1: 65 percent / Amberlyst-15; MeOH / 24 h / 20 °C
9.1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
10.1: dibutyltin oxide / toluene / 6 h / Heating
10.2: 90 percent / CsF / dimethylformamide / 48 h / 20 °C
With
1H-imidazole; methanol; potassium hydroxide; AD-mix-α; amberlyst-15; borane-THF; pyridine-SO3 complex; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; iodine; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; cesium fluoride;
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1.1: Stille cross-coupling / 6.1: Parikh-Doering oxidation;
DOI:10.1021/ol050975u
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 66 percent / CsF / Pd(PPh3)4; CuI / dimethylformamide / 24 h / 45 °C
2.1: 49 percent / AD-mix α / 2-methyl-propan-2-ol; H2O / 24 h / 20 °C
3.1: BH3*THF / tetrahydrofuran / 27 h / 0 - 20 °C
3.2: 75 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0 - 20 °C
4.1: 93 percent / imidazole / dimethylformamide / 24 h / 20 °C
5.1: 72 percent / MeOH; 10-camphorsulfonic acid / CH2Cl2 / 5 h / 0 °C
6.1: 99 percent / SO3*pyridine; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C
7.1: 92 percent / I2; KOH / 0 - 20 °C
8.1: 65 percent / Amberlyst-15; MeOH / 24 h / 20 °C
9.1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
10.1: dibutyltin oxide / toluene / 6 h / Heating
10.2: 90 percent / CsF / dimethylformamide / 48 h / 20 °C
With
1H-imidazole; methanol; potassium hydroxide; AD-mix-α; amberlyst-15; borane-THF; pyridine-SO3 complex; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; iodine; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; cesium fluoride;
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1.1: Stille cross-coupling / 6.1: Parikh-Doering oxidation;
DOI:10.1021/ol050975u
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