3-Deoxy-1α-hydroxycholecalciferol

Abstract

3-Deoxy-1α-hydroxycholecalciferol. The compound is characterized by vitamin D-like activity.

Having thus described the invention, what is claimed is: 
     
       1. 3-deoxy-1α-hydroxycholecalciferol. 
     
     
       2. A method for preparing 3-deoxy-1α-hydroxycholecalciferol which comprises: converting cholesterol into its 6-keto form, 3β-hydroxy-5α-cholestan-6-one;   converting the said keto form into its corresponding ketal, 6,6-ethylenedioxy-5α-cholestan-3β-ol;   oxidizing the said ketal and recovering 6,6-ethylenedioxy-5α-cholestan-3-one;   subjecting the said 3-ketone to bromination and dehydrobromination in sequence and recovering the Δ 1  compound, 6,6-ethylenedioxy-5α-cholest-1-en-3-one;   expoxidizing the said Δ 1  compound and recovering 6,6-ethylenedioxy-1α,2α-epoxy-5α-cholestan-3-one;   treating the recovered epoxy compound with hydrazine and recovering the unsaturated alcohol 6,6-ethylenedioxy-1α-hydroxy-5α-cholest-2-ene;   catalytically reducing the recovered unsaturated alcohol to obtain the ketal 6,6-ethylenedioxy-1α-hydroxy-5α-cholestane;   converting the said ketal to the corresponding ketone and acetylating the ketone to obtain 1α-acetoxy-5α-cholestan-6-one;   treating the acetylated compound with a hydride reducing agent and recovering the alcohol, 1α-acetoxy-5α-cholestan-6β-ol;   dehydrating the recovered alcohol and recovering 1α-acetoxycholest-5-ene;   subjecting the recovered 1α-acetoxycholest-5-ene to allylic bromination and dehydrobromination with trimethyl phosphite and recovering 1α-acetoxy-5,7-cholestadiene;   irradiating the said diene with ultraviolet radiation and recovering 3-deoxy-1α-acetoxy precholecalciferol;   thermally promoting isomerization to 3-deoxy-1α-acetoxy-cholecalciferol, hydrolyzing the said compound and recovering 3-deoxy-1α-hydroxycholecalciferol.   
     
     
       3. A method for preparing 3-deoxy-1α-hydroxycholecalciferol which comprises: hydrolyzing 1α-hydroxycholesterol diacetate and recovering 1α-acetoxycholesterol;   tosylating the recovered compound and extracting 1α-acetoxycholesterol-tosylate from the reaction mixture;   reducing the tosylate with a hydride reducing agent and isolating 1α-hydroxycholest-5-ene from the reduction reaction mixture;   acetylating the isolated compound and recovering 1α-acetoxy-cholest-5-ene;   subjecting the recovered 1α-acetoxycholest-5-ene to allylic bromination and dehydrobromination with trimethyl phosphite and recovering 1α-acetoxy-5,7-cholestadiene;   irradiating the said diene with ultraviolet radiation and recovering 3-deoxy-1α-acetoxy-precholecalciferol;   thermally promoting isomerization to 3-deoxy-1α-acetoxy-cholecalciferol, hydrolyzing the said compound and recovering 3-deoxy-1α-hydroxycholecalciferol. .Iadd. 4. 1α-acetoxy-cholest-5-ene. .Iaddend..Iadd. 5. 1α-acetoxy-5,7-cholestadiene. .Iaddend.