Technology Process of 2,2-Dimethyl-propionic acid (3R,6R)-6-{(Z)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-propenyl}-5,5-bis-ethylsulfanyl-tetrahydro-pyran-3-yl ester
There total 14 articles about 2,2-Dimethyl-propionic acid (3R,6R)-6-{(Z)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-propenyl}-5,5-bis-ethylsulfanyl-tetrahydro-pyran-3-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 6 steps
1: 2) camphersulfonic acid / 1) THF, 80 deg C, 4 h, 2) CH2Cl2, 25 deg C, 12 h
2: 100 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
3: 1) ozone, 2) NaBH4 / 1) CH2Cl2, -78 deg C, 2 h, 2) MeOH, 0 deg C, 2 h
4: 84 percent / I2, PPh3, imidazole / acetonitrile / 0.5 h / 25 °C
5: 90 percent / acetonitrile / 48 h / 80 °C
6: 1) n-BuLi / 1) THF, -78 deg C, 1 h, 2) HMPA, -78 deg C - 25 deg C, 18 h
With
1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; camphor-10-sulfonic acid; iodine; ozone; triphenylphosphine;
In
dichloromethane; acetonitrile;
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 100 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
2: 1) ozone, 2) NaBH4 / 1) CH2Cl2, -78 deg C, 2 h, 2) MeOH, 0 deg C, 2 h
3: 84 percent / I2, PPh3, imidazole / acetonitrile / 0.5 h / 25 °C
4: 90 percent / acetonitrile / 48 h / 80 °C
5: 1) n-BuLi / 1) THF, -78 deg C, 1 h, 2) HMPA, -78 deg C - 25 deg C, 18 h
With
1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; iodine; ozone; triphenylphosphine;
In
dichloromethane; acetonitrile;
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 86 percent / pyridinium dichromate / CH2Cl2 / 6 h / 25 °C
2: 88 percent / NaI, NaOAc, HOAc / acetone / 1 h / 25 °C
3: 74 percent / BF3*OEt2 / CH2Cl2 / 1 h / -40 °C
4: 84 percent / NEt3 / CH2Cl2 / 18 h / 25 °C
5: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C
6: 75 percent / SO3*py, NEt3 / CH2Cl2; dimethylsulfoxide / 1 h / 0 °C
7: 1) n-BuLi / 1) THF, -78 deg C, 1 h, 2) HMPA, -78 deg C - 25 deg C, 18 h
With
dipyridinium dichromate; n-butyllithium; pyridine-SO3 complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium acetate; acetic acid; triethylamine; sodium iodide;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetone;
