344798-32-9Relevant articles and documents
A stereospecific synthesis of 24(S)-hydroxyvitamin D2, a prodrug for 1α,24(S)-dihydroxyvitamin D2
Coutts, Lisa D.,Geiss, William B.,Gregg, Brian T.,Helle, Mark A.,King, Chi-Hsin R.,Itov, Zinovy,Mateo, Mary E.,Meckler, Harold,Zettler, Mark W.,Knutson, Joyce C.
, p. 246 - 255 (2013/09/06)
This contribution describes the first stereospecific synthesis of 24(S)-hydroxyvitamin D2 (1), a metabolite of vitamin D2. This metabolite acts as a prodrug for 1α,24(S)-dihydroxyvitamin D2 (2), which is under development for treatment of various diseases characterized by cellular hyperproliferation. The key step of the synthesis involves the Wittig-Horner olefination of (S)-2,3-dimethyl-2-triethysilyloxybutyraldehyde (17) and a vitamin D2 phosphine oxide derivative (22). The synthesis of the requisite aldehyde started with the commercially available L-(+)-valine and was completed in seven steps. The vitamin D2 phosphine oxide derivative was synthesized in seven steps starting from vitamin D2.