131233-69-7Relevant academic research and scientific papers
Syntheses of D-MYO-inositol-1,2,6-trisphosphate and -2,6-bisphosphate
Chung, Sung-Kee,Yu, Seok-Ho,Chang, Young-Tae
, p. 385 - 390 (1998)
A D-myo-inositol derivative (3), obtained from methyl α-D-glucopyranoside by Ferner rearrangement, was efficiently transformed to D-myo-inositol 1,2,6-trisphosphate (1, α-trinositol) and D-myo-inositol 2,6-bisphosphate (2).
Efficient syntheses of chiral myo-inositol derivatives-key intermediates in glycosylphosphatidylinositol (GPI) syntheses
Yu, Fei,Guo, Zhongwu
scheme or table, p. 3852 - 3855 (2010/03/02)
A facile and effective method was developed for large-scale syntheses of myo-inositol derivatives with the 1,2,6-O-positions differentiated from each other and from other positions as well. The syntheses started from methyl α-d-glucopyranoside, and the ke
Synthesis of differentially protected myo- and chiro-inositols from D-xylose: Stereoselectivity in intramolecular SmI2-promoted pinacol reactions
Luchetti, Giovanni,Ding, Kejia,Kornienko, Alexander,D'Alarcao, Marc
experimental part, p. 3148 - 3154 (2009/04/07)
Methods for the enantioselective conversion of D-xylose into differentially protected myo-inositol and L-chiro-inositol have been developed. The key transformation is a highly diastereoselective intramolecular SmI 2-promoted pinacol coupling. T
Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers
Takahashi,Kittaka,Ikegami
, p. 2705 - 2716 (2007/10/03)
The various inositol polyphosphates have been found to trigger many important biological processes. Although the knowledge of this phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion of 6-O-acetyl-5-enopyranosides into the corresponding substituted cyclohexanones (Ferrier-II rearrangement) was found to proceed efficiently with a catalytic amount of palladium dichloride. Stereoselective reduction of β-hydroxy ketones obtained provided the precursors to all inositol diastereoisomers in good to excellent yields and with high stereoselectivities. Good accessibility of these enantiomerically pure inositol diastereoisomers results in the efficient syntheses of D-myo-inositol 1,4,5-trisphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate.
Ready routes to key myo-inositol component of GPIs employing microbial arene oxidation or Ferrier reaction
Jia, Zhaozhong J.,Olsson, Lars,Fraser-Reid, Bert
, p. 631 - 632 (2007/10/03)
Microbial arene oxidation or Ferrier reaction of enol acetates provides versatile complementary routes that greatly facilitate preparation of inositol synthon(s) for GPI assembly.
Synthesis of optically active myo-inositol derivatives starting from phytic acid
Blum, Corinne,Rehnberg, Nicola,Spiess, Bernard,Schlewer, Gilbert
, p. 163 - 168 (2007/10/03)
Phytic acid treated with Baker's yeast gave D-myo-inositol-1,2,6-tris(phosphate) (α-trinositol) which was transformed into (+)-D-1,2-O-isopropylidene-myo-inositol and (-)-D-4,5-tri- O-benzyl-myo-inositol, two key intermediates in the synthesis of optically active myo-inositol derivatives and related compounds.
The synthesis and resolution of (+/-)-1,5,6-tri-O-benzyl-myo-inositol
Desai, Trupti,Fernandez-Mayoralas, Alfonso,Gigg, Jill,Gigg, Roy,Payne, Sheila
, p. 105 - 123 (2007/10/02)
Racemic 1,5,6-O-benzyl-myo-inositol was prepared by five routes and converted into 1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol, the camphanates of which were readily separated by chromatography.The absolute configurations of the chiral derivative
