Direct C-1 Hydroxylation of Vitamin D Compounds: Convenient Preparation of 1α -hydroxyvitamin D3, 1α ,25-dihydroxyvitamin D3, and 1α -hydroxyvitamin D2
An efficient procedure for the direct C-1 hydroxylation of vitamin D compounds has been developed. The method involves conversion of vitamin D3tosylates to 3,5-cyclovitamin D derivatives, allylic oxidation with selenium dioxide, and acid-catalyzed solvolysis to the 1α -hydroxyvitamin D analogs. When...
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| Published in | Proceedings of the National Academy of Sciences - PNAS Vol. 75; no. 5; pp. 2080 - 2081 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
National Academy of Sciences of the United States of America
01.01.1978
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| Subjects | |
| Online Access | Get full text |
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| Abstract | An efficient procedure for the direct C-1 hydroxylation of vitamin D compounds has been developed. The method involves conversion of vitamin D3tosylates to 3,5-cyclovitamin D derivatives, allylic oxidation with selenium dioxide, and acid-catalyzed solvolysis to the 1α -hydroxyvitamin D analogs. When applied to vitamin D3, 25-hydroxyvitamin D3, and vitamin D2, this sequence gives the corresponding 1α -hydroxylated derivatives in 10-15% yield. |
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| AbstractList | An efficient procedure for the direct C-1 hydroxylation of vitamin D compounds has been developed. The method involves conversion of vitamin D3tosylates to 3,5-cyclovitamin D derivatives, allylic oxidation with selenium dioxide, and acid-catalyzed solvolysis to the 1α -hydroxyvitamin D analogs. When applied to vitamin D3, 25-hydroxyvitamin D3, and vitamin D2, this sequence gives the corresponding 1α -hydroxylated derivatives in 10-15% yield. |
| Author | Hamer, David E. Paaren, Herbert E. DeLuca, Hector F. Schnoes, Heinrich K. |
| Author_xml | – sequence: 1 givenname: Herbert E. surname: Paaren fullname: Paaren, Herbert E. – sequence: 2 givenname: David E. surname: Hamer fullname: Hamer, David E. – sequence: 3 givenname: Heinrich K. surname: Schnoes fullname: Schnoes, Heinrich K. – sequence: 4 givenname: Hector F. surname: DeLuca fullname: DeLuca, Hector F. |
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| ContentType | Journal Article |
| DOI | 10.1073/pnas.75.5.2080 |
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| Snippet | An efficient procedure for the direct C-1 hydroxylation of vitamin D compounds has been developed. The method involves conversion of vitamin D3tosylates to... |
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| SubjectTerms | Acetates Cholecalciferols Isomers Ketones Oxidation Research fellowships Solvolysis Vitamin D |
| Title | Direct C-1 Hydroxylation of Vitamin D Compounds: Convenient Preparation of 1α -hydroxyvitamin D3, 1α ,25-dihydroxyvitamin D3, and 1α -hydroxyvitamin D2 |
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