Synthesis of flavonoid 2-deoxyglucosides via the Mitsunobu reaction. Issue 42 (17th October 2018)

• Record Type: Journal Article
• Authors: Han, Ziyi; Zheng, Zhiwei; Cai, Li; Zhou, Dandan; Li, Changsheng; Sui, Qiang; Liu, Shuai; Gao, Qi
• Is Part Of: Tetrahedron letters. Volume 59:Issue 42(2018)
• Page Start: 3773
• Page End: 3776
• Publication Date: 2018-10-17
• Subjects: Flavonoid glycosides -- Synthesis -- Mitsunobu reaction -- Glycosylation -- Stereoselectivity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.09.008
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Glycosylation of 7-OH flavonoids was achieved via the Mitsunobu reaction. Various flavonoid 2-deoxyglucosides were generated. Stereoselectivity was observed as mainly controlled by the sugar protecting groups. Abstract: The Mitsunobu reaction of flavonoids and 3, 4, 6-tri- O -acetyl-2-deoxy-d -glucopyranose or 3, 4, 6-tri- O -benzyl-2-deoxy-d -glucopyranose is a very effective method for the stereoselective synthesis of flavonoid 2-deoxyglucosides. Since there is no C2 substituent on the sugar moieties, the observed α- or β-stereoselectivity was mainly controlled by the (acetyl or benzyl) protecting groups. Possible mechanistic insights are offered to explain the dual stereoselectivity.