Prearranged Glycosides, Part 12, Intramolecular Mannosylations of ...

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2674 Helvetica Chimica Acta ± Vol. 83 2000) PhCH 2); 4.58 d, J ˆ 10.9, 1 H, PhCH 2); 4.52 ± 4.45 m, 1 H, PhCH 2); 4.49 br. dd, J5,6a) ˆ 4.6, J6a,6b) ˆ 11.7, 2 H C6)); 4.13 t, J4,5) ˆ 9.4, H C4)); 4.12 ± 4.07 m, H C4'), H C5')); 4.09 ± 4.03 m, H C5)); 4.03 ± 3.95m, H C3')); 3.97 ± 3.92 m, H C2')). 13 C-NMR CDCl 3): 166.5, 166.3, 166.2, 166.1 PhCO); 99.3 J1',H C1')) ˆ 172.0, C1')); 95.1 C1)); 79.0 C3')); 75.4 C3)); 75.3 C2')); 74.9 PhCH 2); 74.7 C4)); 74.2 C4')); 72.3, 72.2 PhCH 2); 71.6 C2)); 71.5C5')); 69.7 PhCH 2); 68.5C5)); 63.8 C6)); 63.2 C6')). Anal. calc. for C 68H 62O 15 1119.24): C 72.97, H 5.58; found: C 73.05, H 5.60. We thank Dr. H. Schmickler, I. Hoven, and C. Schmitz for performing NMR spectroscopy and elemental analyses. This work was financially supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. REFERENCES [1] F. Barresi, O. Hindsgaul, J. Am. Chem. Soc. 1991, 113, 9376. [2] F. Barresi, O. Hindsgaul, Synlett 1992, 759. [3] F. Barresi, O. Hindsgaul, Can. J. Chem. 1994, 72, 1447. [4] Y. Ito, T. Ogawa, Angew. Chem. 1994, 106, 1843; Angew. Chem., Int. Ed. 1994, 33, 1765. [5] A. Dan, Y. Ito, T. Ogawa, J. Org. Chem. 1995, 60, 4680. [6] A. Dan, Y. Ito, T. Ogawa, Tetrahedron Lett. 1995, 36, 7487. [7] A. Dan, Y. Ito, T. Ogawa, Carbohydr. Lett. 1996, 1, 469. [8] Z.-W. Guo, Y. Nakahara, T. Ogawa, Tetrahedron Lett. 1997, 38, 4799. [9] Y. Ito, T. Ogawa, J. Am. Chem. Soc. 1997, 119, 5562. [10] A. Dan, M. Lergenmüller, M. Amano, Y. Nakahara, T. Ogawa, Y. Ito, Chem. ± Eur. J. 1998, 4, 2182. [11] M. Lergenmüller, T. Nukada, K. Kuramochi, A. Dan, T. Ogawa, Y. Ito, Eur. J. Org. Chem. 1999, 1367. [12] G. Stork, G. Kim, J. Am. Chem. Soc. 1992, 114, 1087. [13] M. Bols, J. Chem. Soc., Chem. Commun. 1992, 913. [14] M. Bols, T. Skrydstrup, Chem. Rev. 1995, 95, 1253. [15] M. Bols, Acta Chem. Scand. 1996, 50, 931. [16] G. Stork, J. J. LaClair, J. Am. Chem. Soc. 1996, 118, 247. [17] S. Inaba, M. Yamada, T. Yoshino, Y. Ishido, J. Am. Chem. Soc. 1973, 95, 2062. [18] T. Iimori, T. Shibazaki, S. Ikegawa, Tetrahedron Lett. 1996, 37, 2267. [19] G. Scheffler, R. R. Schmidt, Tetrahedron Lett. 1997, 38, 2943. [20] M. E. Behrendt, R. R. Schmidt, Tetrahedron Lett. 1993, 34, 6733. [21] C. Mukai, T. Itoh, M. Hanaoka, Tetrahedron Lett. 1997, 38, 4595. [22] T. Ogawa, Y. Takahashi, Carbohydr. Res. 1985, 138, C5. [23] Y. Takahashi, T. Ogawa, Carbohydr. Res. 1987, 164, 277. [24] M. Mori, Y. Ito, T. Ogawa, Tetrahedron Lett. 1989, 30, 1273. [25] T. Ziegler, R. Lau, Tetrahedron Lett. 1995, 36, 1417. [26] R. Lau, G. Schüle, U. Schwaneberg, T. Ziegler, Liebigs Ann. Chem. 1995, 1745. [27] T. Ziegler, G. Lemanski, A. Rakoczy, Tetrahedron Lett. 1995, 36, 8973. [28] S. Valverde, A. M. GoÂ mez, A. HernaÂndez, B. HerrandoÂ n, J. C. LoÂ pez, J. Chem. Soc., Chem. Commun. 1995, 2005. [29] S. Valverde, A. M. GoÂ mez, J. C. LoÂ pez, B. HerrandoÂ n, Tetrahedron Lett. 1996, 37, 1105. [30] G. Schüle, T. Ziegler, Liebigs Ann. Chem. 1996, 1599. [31] T. Ziegler, A. Ritter, J. Hürttlen, Tetrahedron Lett. 1997, 38, 3715. [32] H. Yamada, K. Imamura, T. Takahashi, Tetrahedron Lett. 1997, 38, 391. [33] U. Huchel, R. R. Schmidt, Tetrahedron Lett. 1998, 39, 7693. [34] T. Ziegler, G. Lemanski, Eur. J. Org. Chem. 1998, 163. [35] T. Ziegler, G. Lemanski, Angew. Chem. 1998, 110, 3367; Angew. Chem., Int. Ed. 1998, 37, 3129. [36] R. J. Tennant-Eyles, B. G. Davis, A. J. Fairbanks, Chem. Commun. 1999, 1037. [37] A. Geyer, M. Müller, R. R. Schmidt, J. Am. Chem. Soc. 1999, 121, 6312. [38] M. Müller, U. Huchel, A. Geyer, R. R. Schmidt, J. Org. Chem. 1999, 64, 6190. [39] T. Ziegler, R. Dettmann, Ariffahdillah, U. Zettl, J. Carbohydr. Chem. 1999, 18, 1079. [40] G. Lemanski, T. Ziegler, Eur. J. Org. Chem. 2000, 181. [41] G. Lemanski, T. Ziegler, Tetrahedron 2000, 56, 563. [42] G. Lemanski, T. Lindenberg, H. Fakhrnabavi, T. Ziegler, J. Carbohydr. Chem. 2000, 19, 727.
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