220151-07-5

Upstream product

• 40653-15-4 methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 
• 108-24-7 acetic anhydride 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 220198-41-4 L-2-O-acetyl-4,5,6-tri-O-benzyl-chiro-inositol 
• 38876-99-2 1L-chiro-inositol 
• 220151-15-5 (1R,2R,3R,4R,5S)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate 

Relevant academic research and scientific papers

Reducing the conformational flexibility of carbohydrates: Locking the 6-hydroxyl group by cyclopropanes

The 6-hydroxyl group of hexopyranosides was stereochemically locked by the spiroannelation of a cyclopropane unit at C-5. The corresponding glucose and mannose derivatives were prepared and their behaviour in glycosidation reactions was studied.

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.