220198-38-9

Upstream product

• 220151-05-3 (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galacto-hex-5-enopyranoside 
• 342789-67-7 (E)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galacto-hex-5-enopyranoside 
• 220152-90-9 (1S,2S,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 
• 134680-55-0 methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside 

Downstream Products

• 488-55-1 muco-inositol 

Relevant academic research and scientific papers

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.

Novel synthesis of enantiomerically pure natural inositols and their diastereomers

A novel synthesis of all stereoisomers of natural inositols has been developed. The key strategy is the stereoselective reduction of substituted β-hydroxy cyclohexanones which are prepared from a variety of 6-O-acetyl 5- enopyranosides via Ferrier-II reaction catalyzed by palladium chloride. The utility of this approach is demonstrated by the synthesis of D-myo-inositol 1,4,5-tris(phosphate)(IP3).