A Concise and Efficient Route to 2α-(ω-Hydroxyalkoxy)-1α,25-dihydroxyvitamin D3: Remarkably High Affinity to Vitamin D Receptor1
- 1 August 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (17) , 2619-2622
- https://doi.org/10.1021/ol006222j
Abstract
A convenient and potentially valuable synthetic approach to the novel 2α-functionalized 1α,25-dihydroxyvitamin D3 [1α,25(OH)2D3] derivatives (1a−c), which are the C2-epimer of ED-71 and its analogues, has been developed. The C2α-modified ring A precursors (1,7-enynes 16, n = 0, 1, and 2) were constructed stereoselectively starting from d-glucose in high yield. In the synthesized 2α-(ω-hydroxyalkoxy)-1α,25(OH)2D3 derivatives, 1a and 1b showed a greater binding affinity to vitamin D receptor (VDR), up to 1.8 times that of the native hormone.Keywords
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