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Compounds effective in inducing cell differentiation and process for preparing same

  • US 4,927,815 A
  • Filed: 04/29/1988
  • Issued: 05/22/1990
  • Est. Priority Date: 04/29/1988
  • Status: Expired due to Fees
First Claim
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1. A process for the preparation of vitamin D compounds having the general structure:

  • ##STR8## where X and Y, which may be the same or different, are selected from the group consisting of hydrogen and a hydroxy-protecting group, and where R is selected from the group consisting of alkyl, fluoro-substituted alkyl, hydroxy-substituted alkyl, hydroxy and fluoro-substituted alkyl, hydroxy-protected hydroxy-substituted alkyl and hydroxy-protected hydroxy- and fluoro-substituted alkyl, which comprises treating a vitamin D-22-tosylate derivative, of the general structure;

    ##STR9## where X and Y are selected from the group consisting of hydrogen and hydroxy-protecting groups, with an alkylphenylsulfone derivative of the general structure;

    
    
    space="preserve" listing-type="equation">Ph--SO.sub.2 --CH.sub.2 --Rwherein R is selected from the group consisting of alkyl, fluoro-substituted alkyl, hydroxy-substituted alkyl, and hydroxy- and fluoro-substituted alkyl, any hydroxy group present being preferably derivatized by hydroxy-protecting groups, thereby obtaining a side chain sulfone adduct, having the following general structure;

    ##STR10## wherein X, Y and R represent the groupings defined above, and reductively desulfonating said side chain sulfone adduct so as to obtain the corresponding vitamin D compound, and, optionally removing the hydroxy-protecting groups present.

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