The New Observation of Intramolecular Acyl Transfer from Aglycon to Sugar of C-Glycoside. The Regioselective and Single Step Acylation of 2′-Hydroxyl Group of Free C-Glucopyranoside.

Author:

Park Man Ki,Park Jeong Hill,Cho Sool Yeon,Shin Young Geun,Jung Jae-Kyung,Suh Young-Ger

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference7 articles.

1. Recent developments in the synthesis of C-glycosides

2. a) Conner, J.M.; Gray, A.I.; Reynolds, T.; Waterman, P.G. Phytochemistry 1990, 29, 941–944. b) Mebe, P.P. Phytochemistry 1987, 26, 2646–2647. c)Gramatica, P.; Monti, D.; Speranza, G.; Manitto, P. Tetrahedron Lett. 1982, 23, 2423–2424. Makino, K.; Yagi, A.; Nishioka, I. Chem. Pharm. Bull. 1974, 22, 1565–1570. Speranza, G.; Martignoni, A.; Mantto, P. J. Nat. Prod. 1988, 51, 588–590. d) Conner, J.M.; Gray, A.I.; Reynolds, T.; Waterman, P.G. Phytochemistry 1989, 28, 3551–3553. e) Speranza, G.; Dada, G.; Lunazzi, L.; Gramatica, P.; Manitto, P. Phytochemistry 1986, 25, 2219–3333. f) Speranza, G.; Gramatica, P.; Dada, G.; Manitto, P. Phytochemistry 1985, 24, 1571–1573.

3. Chemistry, Occurrence and Biosynthesis ofC-Glycosyl Compounds in Plants

4. For selective acylations of the secondary hydroxy group of O-glycosides, see: a) Williams, J.M.; Richardson, A.C. Tetrahedron 1967, 23, 1369–1378. b) Pulido, R.; Gotor, V. Carbohydr. Res. 1994, 252, 55–68 and references cited therein. c) Haines, A.H.: Relative Reactivities of Hydroxyl Groups in Carbohydrates. In Advances in Carbohydrate Chemistry and Biochemistry; Tipson, R.S.; Horton D. Eds.; Academic Press: New York, 1976; vol 33, pp. 101–107. d) Slife, C.W.; Nashed, M.A.; Anderson, L. Carbohydr. Res. 1981, 93, 219–230.

5. Winters, W.D.: Proceedings of the International Congress of Phytotherapy Phytotherapy Research 1993, 7 (Special Issue), S1–S72.

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