Cyanomethyl Ether as an Orthogonal Participating Group for Stereoselective Synthesis of 1,2-trans-β-O-Glycosides was written by Molla, Mosidur Rahaman;Das, Pradip;Guleria, Kanika;Subramanian, Ranga;Kumar, Amit;Thakur, Rima. And the article was included in Journal of Organic Chemistry in 2020.Synthetic Route of C12H20O6 This article mentions the following:
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. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Synthetic Route of C12H20O6).
(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Commercial tetrahydrofuran contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds. Although tetrahydrofuran is traditionally dried by distillation from an aggressive desiccant, molecular sieves are superior.Synthetic Route of C12H20O6
Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem