123836-61-3Relevant 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; 51-52, (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 73-74, (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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, (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 51-52, (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.
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.
Chemical conversion of vitamin D3 to its 1,25-dihydroxy metabolite
Kiegiel,Wovkulich,Uskokovic
, p. 6057 - 6060 (2007/10/02)
Vitamin D3 (6) has been converted to the 1,25-dihydroxy vitamin D3 metabolite (1) and the 1α-fluoro derivative 2 via a new process. The strategy involved the cleavage of the ring A portion from the CD portion in vitamin D3
