123836-63-5Relevant academic research and scientific papers
SYNTHESIS OF 1α-FLUORO-25-HYDROXY-16-23E-DIENE-26,27-BISHOMO-20-EPI-CHOLECALCIFEROL
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Page/Page column 15; 46-47; 52-53, (2008/12/07)
The invention provides a method of producing 20-methyl vitamin D3 compounds of formula (I). The method includes hydroxylation, carbonyl reduction, fluoride substitution, epoxide deoxygenation, and Wittig-type couplings.
NOVEL METHOD
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Page/Page column 69-70; 75, (2008/06/13)
There is provided a method of prevention of adhesions, eg surgical adhesions, which comprises using a vitamin D compound.
NOVEL METHOD
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Page/Page column 27; 36-37, (2010/11/28)
The invention provides for the use of Vitamin D compounds such as 1-alpha-fluoro-25- hydroxy-16,23E-diene-26,27-bishomo-20-epi-cholecalciferol, in the prevention or treatment of prostate cancer.
SYNTHESIS OF 1α-FLUORO-25-HYDROXY-16-23E-DIENE-26,27-BISHOMO-20-EPI-CHOLECALCIFEROL
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Page/Page column 52-53; 58-59, (2008/06/13)
The invention provides a method of producing 20-methyl vitamin D3 compounds of formula (I). The method includes allylic and olefin oxidation, decarbonylation, carbonyl reduction, fluoride substitution, epoxide deoxygenation, and Wittig-type couplings.
Improved preparation of A-ring phosphine oxides for the synthesis of vitamin D analogs
Daniewski, Andrzej R.,Garofalo, Lisa M.,Kabat, Marek M.
, p. 3031 - 3039 (2007/10/03)
A new, high yielding, two-step process for the preparation of A-ring phospine oxides from allyl alcohols, useful for the synthesis of vitamin D analog, is described, in which triphos-gene and diphenylphosphine oxide are used for chlorination and subsequen
Efficient synthesis of 1α-fluoro A-ring phosphine oxide, a useful building block for vitamin D analogues, from (S)-carvone via a highly selective palladium-catalyzed isomerization of dieneoxide to dieneol
Kabat,Garofalo,Daniewski,Hutchings,Liu,Okabe,Radinov,Zhou
, p. 6141 - 6150 (2007/10/03)
The 1α-fluoro A-ring phosphine oxide 1, a useful building block for fluorinated vitamin D analogues, was synthesized from (S)-carvone in 13 synthetic steps, and only five isolations, in 22% overall yield. In the key synthetic step, a highly selective palladium-catalyzed isomerization of dieneoxide 18 to dieneol 20 was achieved using an appropriately selected fluorinated alcohol as a catalytic proton source.
Efficient fluorination with tetrabutylammonium dihydrogen trifluoride in a novel approach toward 1-α-fluoro-25-hydroxy-vitamin D3 analogues
Barbier, Pierre,Mohr, Peter,Muller, Marc,Masciadri, Raffaello
, p. 6984 - 6989 (2007/10/03)
The known, but hardly accessible, A-ring phosphine oxide 20, a building block for 1-α-fluoro-25-hydroxy-vitamin D3, was prepared by a new route in gram amounts from (S)-(+)-carvone in 20 steps and 0.6% overall yield. Fluorine was introduced at an early stage by the completely regio-and stereoselective trans-diaxial opening of key-epoxide 5 with neat tetrabutylammonium dihydrogen trifluoride at 95 °C. The required 2-carbon chain extension of cyclohexanol 13 was accomplished in moderate yield via S(N)' substitution with cesium phenylselanyl acetate followed by Ireland- Claisen rearrangement of the resulting ester 15. Spontaneous elimination of the derived phenyl selenoxide led stereorandomly to a 1:1 mixture of dienoates E/Z-17, which was transformed into 20 as previously described.
