Molla, Mosidur Rahaman; Das, Pradip; Guleria, Kanika; Subramanian, Ranga; Kumar, Amit; Thakur, Rima published the artcile< Cyanomethyl Ether as an Orthogonal Participating Group for Stereoselective Synthesis of 1,2-trans-β-O-Glycosides>, Application In Synthesis of 4064-06-6, the main research area is tetrazole glycoside cyclization azide cyanide glycoside preparation; disaccharide stereoselective glycosylation thioglycoside glycoside preparation protecting group cyanomethyl.
Stereoselective formation of glycosidic linkages has been the prime focus for contemporary carbohydrate chem. Herein, we report cyanomethyl (CNMe) ether as an efficient and effective participating orthogonal protecting group for the stereoselective synthesis of 1,2-trans-β-O-glycosides. The participating group facilitated good to high β-selective glycosylation with a broad range of electron-rich and electron-deficient glycosyl acceptors. Detailed exptl. and theor. studies reveal the involvement of CNMe ether in the formation of a six-membered imine-type cyclic intermediate for the observed stereoselectivity. Rapid incorporation and selective removal of the CNMe ether group in the presence of benzyl ether and isopropylidene acetal protection have also been reported here. The nitrile group provided an opportunity for the glyco-diversification through further derivatization.
Journal of Organic Chemistry published new progress about Cyclization. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Application In Synthesis of 4064-06-6.
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