PURPOSE: To provide new 26,26,26,27,27,27-hexafluoro-1 α,25-dihydroxycholesterol as an intermediate for the synthesis of a new vitamin D3 deriv. excellent in activity similar to that of vitamin D and useful as a drug for renal osteodystrophy, osteoporosis, etc.
CONSTITUTION: 26,26,26,27,27,27-Hexafluoro-25-hydroxycholesterol-3-THP ether of formula I is hydrolyzed with p-toluenesulfonic acid in a CH2Cl2-methanol mixed solvent, the resultant product is oxidized with dichlorocyanobenzoquinone in dioxane, the resultant compd. of formula II is treated with an alkali hydrogen peroxide and the resultant 1,2-epoxide is reduced with metal lithium and ammonium chloride in an ammonia-THF soln. to obtain the objective 26,26,26,27,27,27- hexafluoro-1 α,25-dihydroxycholesterol.
TANAKA YOKO
IKEGAWA NOBUO
KOBAYASHI YOSHIRO
US4199518A | 1980-04-22 | |||
US4248791A | 1981-02-03 |