106032-59-1Relevant articles and documents
Regioselective phosphorylation of: Myo -inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol
Aiba, Toshihiko,Sato, Masaki,Umegaki, Daichi,Iwasaki, Takanori,Kambe, Nobuaki,Fukase, Koichi,Fujimoto, Yukari
supporting information, p. 6672 - 6675 (2016/07/21)
A regioselective phosphorylation method for myo-inositol was developed by utilizing readily preparable BINOL-derived phosphoramidites. The method also facilitated the complete separation of the diastereomeric products by simple chromatography. Based on this phosphorylation and Ni-catalyzed alkyl-alkyl cross-coupling reaction for long fatty acids, we achieved the first synthesis of a lysophosphatidylinositol, EhPIa having long fatty acid C30:1, as a partial structure of glycosylphosphatidylinositol (GPI) anchor from the cell membrane of a protozoa, Entamoeba histolytica.
Enantiodivergence in small-molecule catalysis of asymmetric phosphorylation: Concise total syntheses of the enantiomeric D-myo-inositol-1-phosphate and D-myo-inositol-3-phosphate
Sculimbrene, Bianca R.,Morgan, Adam J.,Miller, Scott J.
, p. 11653 - 11656 (2007/10/03)
Peptide-based catalysts have been found that catalyze the enantiodivergent phosphorylation of a meso myo-inositol-derived triol (1). The sequential screening of random peptide libraries, followed by the evaluation of a focused library, led to the identifi
Structure of (±)-1,2;4,5-di-o-cyclohexylidene myo-inositol and synthesis of myo-inositol 3-phosphate via its phosphorylation with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one
Spiers, Ian D.,Schwalbe, Carl H.,Blake, Alexander J.,Solomons, Kevin R.H.,Freeman, Sally
, p. 43 - 51 (2007/10/03)
The crystal structure of (±)-1,2;4,5-di-O-cyclohexylidene myo-inositol, refined to R = 2.9%, shows interestingly disordered (flip-flop) hydrogen bonding. The higher reactivity of the 1/3 positions (rather than 4/6) has been evaluated using semi-empirical calculations. This diol has been phosphorylated with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2- oxazaphospholidin-2-one and the diastereoisomer derived from phosphorylation at the 3-position was isolated by crystallisation. Deprotection with TFA/H2O then H2/Pd-C afforded myo-inositol 3-phosphate in only four steps from myo- inositol.