85747-85-9Relevant academic research and scientific papers
Synthesis of 3,4,5,6-tetrakisphosphates of DL-1,2-dideoxy-1,2-difluoro-myo-inositol and DL-1,2-dideoxy-1,2-difluoro-scyllo-inositol as analogues of DL-myo-inositol 3,4,5,6-tetrakisphosphate
Solomons, Kevin R. H.,Freeman, Sally,Poyner, David R.,Yafai, Farid
, p. 1845 - 1851 (2007/10/03)
DL-1,2-Dideoxy-1,2-difluoro-myo-inositol was prepared from DL-3,4,5,6-tetra-O-benzyl-myo-inositol in five steps in an overall yield of 36%. The fluoro substituents were introduced with DAST in separate steps by displacement of hydroxy substituents with inversion of stereochemistry. Difluorination could not be achieved in one step because of competing formation of a 1,4-anhydro derivative. DL-1,2-Dideoxy-1,2-difluoro-scyllo-inositol was prepared in 42% overall yield using similar chemistry, with the required inversion of one stereocentre being accomplished by displacement of a tosyl group with caesium propionate. Both difluoroinositol analogues increased the levels of phytic acid (InsP6) in a skeletal muscle cell line. Each compound was tetraphosphorylated with dibenzyl N,N-diisopropylphosphoramidite in the presence of 1H-tetrazole, with subsequent oxidation of the phosphite with MCPBA. The P-OBn groups were removed by H2/Pd-C, and the sodium salts of the tetrakisphosphates of the difluoroinositol analogues were obtained by cation exchange.
A Synthesis of (-)-1L-1-Deoxy-1-fluoro-myo-inositol; a Compound of Potential Use in sorting out the Phosphatidylinositol Response
Kozikowski, Alan P.,Xia, Yan,Rusnak, James M.
, p. 1301 - 1303 (2007/10/02)
A synthesis of 1L-1-deoxy-1-fluoro-myo-inositol in optically pure form starting from myo-inositol is reported.
SYNTHESIS OF FLUORODEOXYSCYLLOINOSITOL AND PHOSPHATIDYLFLUORODEOXYSCYLLOINOSITOL
Yang, Shu Shu,Beattie, Thomas R.,Shen, T. Y.
, p. 5517 - 5520 (2007/10/02)
Synthesis of 1-fluoro-1-deoxyscylloinositol and 2-fluoro-2-deoxy-1-phosphatidylscylloinositol from myoinositol is described.
