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This is explained by the formation of cationic intermediates of type 88 resulting from the heterolytic opening of the epoxide, and subsequent intramolecular delivery of the carbon nucleophile to the anomeric center giving 89 after aqueous work-up101 (Scheme 29). Scheme 29 One-pot synthesis of a-C-glycosyl compounds from glycals using organoaluminium and organoboron reagents. Seitz and co-workers102 have used Ar3Al and ArMe2Al for the cis-selective opening of 1,2-anhydroarabinose 90, obtaining compound 92 in moderate to good yield (Scheme 30).
Karplus, J. Am. Chem. , 1991, 113, 1553; R. K. Schmidt, M. Karplus and J. W. Brady, J. Am. Chem. , 1996, 118, 541. 32 O. Takahashi, K. Yamasaki, Y. Kohno, R. Ohtaki, K. Ueda, H. Suezawa, Y. Umezawa and M. Nishio, Carbohydr. , 2007, 342, 1202. 33 A. Vila and R. A. Mosquera, J. Comput. , 2007, 28, 1516; M. L. Trapp, J. K. Watts, N. Weinberg and B. M. Pinto, Can. J. , 2006, 84, 692. 34 P. G. Goekjian, T. C. Wu, H. Y. Kang and Y. Kishi, J. Org. , 1987, 52, 4823; Y. Wang, P. G. Goekjian, D. M. Ryckman and Y.
Scheme 38 When methyl 2,3,4,6-tetra-O-benzyl-a-D-galactopyranoside 119 is treated with propargyltrimethylsilane and Me3SiOTf in MeCN, the C-glycosyl allene 120 is obtained. Its ozonolysis provides the a-C-glycosyl aldehyde 121a. Epimerization of 121a with 10% Et3N in isopropanol/CH2Cl2 gives the b-C-glycosyl aldehyde 121b115 (Scheme 39). 4 Use of aryl pyranosides. Fries-type rearrangement. An useful approach to the synthesis of aryl C-glycosyl aromatic compounds is the Fries-type rearrangement of aryl O-glycosides induced by Lewis acids.