137793-96-5Relevant academic research and scientific papers
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
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.
Efficient syntheses of penta-hydroxylated cyclohexanones via PdCl2- mediated Ferrier-II reaction of 6-O-acetyl-5-enopyranosides
Takahashi, Hideyo,Kittaka, Hisae,Ikegami, Shiro
, p. 9703 - 9706 (2007/10/03)
The conversion of 6-O-acetyl-5-enopyranosides into fully oxygenated cyclohexanones was found to proceed efficiently with a catalytic amount of palladium chloride under neutral conditions. This method was proved to be superior in efficacy to the convention
