342789-72-4

Upstream product

• 68102-59-0 2,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 26927-44-6 methyl 2,6-di-O-benzoyl-α-D-glycopyranoside 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 

Downstream Products

• 342789-73-5 methyl 3,4-di-O-(4-methoxybenzyl)-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside 
• 342789-74-6 methyl 6-O-tert-butyldimethylsilyl-2-O-benzyl-3,4-di-O-methoxybenzyl-α-D-glucopyranoside 
• 173911-76-7 methyl (Z)-2-O-benzyl-3,4-di-O-(p-methoxybenzyl)-6-O-acetyl-α-D-glucos-5-enopyranoside 
• 162583-79-1 methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 183170-36-7 methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hexodialdopyranoside (1,5) 

Relevant academic research and scientific papers

Synthesis of glycoaminooxy acid and N-oxyamide-linked glycolipids

Aminooxyl sugar derivatives are versatile building blocks for the generation of various glycoconjugates with interesting bioactivities. We report herein a synthetic method for the preparation of orthogonally protected glycoaminooxy acid from methyl α-d-gl

Benzylation of hydroxy groups with tertiary amine as a base

The benzylation of hydroxy groups in the presence of tertiary amines is described. A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. The importance of solventless conditions was observed. The reaction showed high tolerance to many functional groups including benzoate, even at a reaction temperature of 150 °C. Sodium iodide was found to be an efficient catalyst to accelerate the reaction.

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.