Vitamin D related compounds and processes for their preparation
First Claim
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1. Compounds having the formula:
- ##STR5## where X and Y, which may be the same or different, are each selected from the group consisting of hydrogen, and a hydroxy-protecting group, and where W is selected from the group consisting of CHO, COO-alkyl and COO-aryl.
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Abstract
The invention relates to a method for preparing vitamin D-related compounds and to certain intermediate compounds in such process. The intermediate compounds are characterized by an aldehyde or ester in the C-22 position in the side chain. The presence of such groups permit facile side chain additions for the preparation of vitamin D derivatives.
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17 Claims
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1. Compounds having the formula:
- ##STR5## where X and Y, which may be the same or different, are each selected from the group consisting of hydrogen, and a hydroxy-protecting group, and where W is selected from the group consisting of CHO, COO-alkyl and COO-aryl.
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8)
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9. A compound of the formula:
- ##STR6## wherein R is selected from the group consisting of alkyl, hydroxylated alkyl, hydroxy-protected-hydroxylated alkyl, fluoro-substituted alkyl, fluoro-substituted hydroxylated alkyl and fluoro-substituted hydroxy-protected alkyl, and where X and Y, which may be the same or different, are each selected from the group consisting of hydrogen and a hydroxy-protecting group.
- 10. A method for preparing vitamin D compounds of the formula ##STR7## wherein R is selected from the group consisting of alkyl, hydroxylated alkyl, hydroxy-protected hydroxylated alkyl, fluoro-substituted alkyl, fluoro-substituted hydroxylated alkyl and fluoro-substituted hydroxy-protected alkyl, and where X and Y, which may be the same or different, are each selected from the group consisting of hydrogen and a hydroxy-protecting group, which comprises, treating a C-22-aldehyde compound of the formula ##STR8## where X and Y are as defined above, with a phenylsulfone derivative of the formula
- space="preserve" listing-type="equation">PhSO.sub.2 CH.sub.2 R
wherein R is a group as defined above, in the presence of a strong base and an organic medium, whereby a hydroxy-sulfonyl adduct of the formula ##STR9## is obtained, wherein R, X and Y are as defined above, reducing said adduct to obtain the desired vitamin D compound, and, optionally, removing hydroxy-protecting groups. - View Dependent Claims (11, 12, 13, 14, 15, 16, 17)
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