141611-10-1Relevant articles and documents
Yb(OTf)3-Catalyzed Desymmetrization of myo-Inositol 1,3,5-Orthoformate and Its Application in the Synthesis of Chiral Inositol Phosphates
Padiyar, Laxmansingh T.,Zulueta, Medel Manuel L.,Sabbavarapu, Narayana Murthy,Hung, Shang-Cheng
, p. 11418 - 11430 (2017/11/10)
A variety of inositol phosphates including myo-inositol 1,4,5-trisphosphate, which is a secondary messenger in transmembrane signaling, were selectively synthesized via Yb(OTf)3-catalyzed desymmetrization of myo-inositol 1,3,5-orthoformate using a proline-based chiral anhydride as an acylation precursor. The investigated catalytic system could regioselectively differentiate the enantiotopic hydroxy groups of myo-inositol 1,3,5-orthoformate in the presence of a chiral auxiliary. This key step to generate a suitably protected chiral myo-inositol derivatives is described here as a unified approach to access inositol phosphates.
A type 2 Ferrier rearrangement-based synthesis of d-myo-inositol 1,4,5-trisphosphate
Keddie, Neil S.,Bultynck, Geert,Luyten, Tomas,Slawin, Alexandra M.Z.,Conway, Stuart J.
experimental part, p. 857 - 866 (2009/09/30)
The synthesis of d-myo-inositol 1,4,5-trisphosphate (InsP3) from methyl α-d-glucopyranose, via a type 2 Ferrier rearrangement is reported. A key intermediate in this synthesis possesses orthogonal protecting groups at the 1-, 4- and 5-position, making it a versatile starting point for the synthesis of unnatural InsP3 derivatives. Biological evaluation of the synthetic InsP3 demonstrates that this compound evokes selective Ca2+ release via activation of InsP3 receptors.
Regioselective phosphorylation of vicinal 3,4-hydroxy myo-inositol derivative promoted practical synthesis of D-PtdIns(4,5)P2 and D-Ins(1,4,5)P3
Han, Fushe,Hayashi, Minoru,Watanabe, Yutaka
, p. 7703 - 7711 (2007/10/03)
The reactivity of 3 and 4-OH in 3,4-diol myo-inositol derivatives were observed through the phosphorylation, acylation and silylation. The results indicated that 3-OH is much more reactive than 4-OH, giving regiospecifically 3-mono-functionalized products