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...

Full description

Saved in:
Bibliographic Details
Published inProceedings of the National Academy of Sciences - PNAS Vol. 75; no. 5; pp. 2080 - 2081
Main Authors Paaren, Herbert E., Hamer, David E., Schnoes, Heinrich K., DeLuca, Hector F.
Format Journal Article
LanguageEnglish
Published National Academy of Sciences of the United States of America 01.01.1978
Subjects
Acetates
Cholecalciferols
Isomers
Ketones
Oxidation
Research fellowships
Solvolysis
Vitamin D
Online AccessGet full text

Cover

More Information
Summary: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.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.75.5.2080