190060-68-5

Upstream product

• 220198-32-3 D-3-O-acetyl-1,5,6-tri-O-benzyl-epi-inositol 
• 131146-89-9 (+/-)-1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 137793-90-9 (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside 
• 137793-91-0 (E)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside 
• 137793-96-5 (1R,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-6-oxocyclohexyl acetate 
• 83051-88-1 methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 488-58-4 epi-Inositol 

Relevant academic research and scientific papers

Reactions of the ketone derived from (±)-3,4,5-tri-O-benzyl-1,2-O-isopropylidene-myo-inositol: Preparation of racemic derivatives of epi-inositol and of 4-C-methyl-epi-[(±)-iso-laminitol] and 4-C-methyl-myo-inositol [(±)-laminitol]

Oxidation of (±)-3,4,5-tri-O-benzyl-1,2-O-isopropylidene-myo-inositol with the pyridine-SO3, complex in methyl sulfoxide gave the ketone which was reduced with sodium borohydride to give almost exclusively the corresponding epi-inositol derivative. Reaction of the ketone with diazomethane gave an epoxide which was reduced with lithium aluminium hydride to give a 4-C-methyl-myo-inositol derivative and reaction of the ketone with methyl magnesium iodide gave the isomeric 4-C-methyl-epi-inositol derivative.

Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers

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.