C-Glycosylation of tri-O-benzyl-2-deoxy-D-glucose: synthesis of naphthyl-substituted 3, 6-dioxabicyclo [3.2. 2] nonanes

MA Brimble, TJ Brenstrum

Index: Brimble; Brenstrum Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 14 p. 1612 - 1623

Full Text: HTML

Citation Number: 20

Abstract

The syntheses of naphthol 7, naphthol 8, naphthol 11 and naphthol 12 are described, starting from juglone 13. C-Glycosylation of naphthol 8 with benzyl-protected glycosyl donor 10 using trimethylsilyl trifluoromethanesulfonate and silver perchlorate or boron trifluoride– diethyl ether affords rearranged product 36 in which the glycosyl donor has undergone an unusual 1, 6-hydride shift. Use of the corresponding naphthol 12 as the glycosyl acceptor ...