Synthesis of (22R)- and (22S)-22,25-dihydroxyvitamin D3 and determination of their biological activity.

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Abstract
Bisnorcholenal 3-tetrahydropyranyl ether, obtained from bisnorcholenic acid in 3 steps, was coupled with lithium acetylide derived from 2-methyl-3-butyn-2-ol tetrahydropyranyl ether to give in 74% yield a 1:1 mixture of the cholest-5-ene-3.beta.,22,25-trihydroxy-23-yne 3,25-bis(tetrahydropyranyl)ethers. After resolution of the C-22 epimers and determination of their configurations, both isomers were converted to 22,25-dihydroxycholesterol 3,22-diacetates, and to 25-hydroxy-22-methoxycholesterol 3-acetate. These compounds were converted to (22R)- and (22S)-22,25-dihydroxyvitamin D3, and to 25-hydroxy-22-methoxyvitamin D3, through the corresponding cholest-5,7-diene-3.beta.,22,25-triol 3,22-diacetates and cholest-5,7-diene-22-methoxy-3.beta.,25-diol 3-acetates. According to preliminary biological tests [intestinal Ca transport and serum Ca concentration of vitamin D-deficient rats], 22,25-(OH)2D3 and 22-CH3O-25-OH-D3 have neither vitamin D activity nor antivitamin D activity.

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