Intramolecular glycoside bond formation - A rigid spacer concept for the diastereoselective linkage between glycosyl donor and acceptor

Tetrahedron Letters

Volumn 39, Issue 42, 1998, Pages 7693-7694

  Huchel, Ursula ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; GLYCOSIDE; META XYLENE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; DIASTEREOISOMER; GLYCOSYLATION; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032532582     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01664-5     Document Type: Article

References (25)

1. [1] Barresi F, Hindsgaul OJ. J. Am. Chem. Soc. 1991;113:9376-9377; Synlett 1992;759-761; Can. J. Chem. 1994;72:1447-1465.
2. [1] Barresi F, Hindsgaul OJ. J. Am. Chem. Soc. 1991;113:9376-9377; Synlett 1992;759-761; Can. J. Chem. 1994;72:1447-1465.
3. [1] Barresi F, Hindsgaul OJ. J. Am. Chem. Soc. 1991;113:9376-9377; Synlett 1992;759-761; Can. J. Chem. 1994;72:1447-1465.
4. [2] Preuss R, Jung KH, Schmidt RR. Liebigs Ann. Chem. 1992;377-382.
5. [3] Stork, G, Kim GJ. J. Am. Chem. Soc. 1992;114:1087-1088; Bols M. J. Acta Chem. Scand. 1996;50:931-937; Ito Y, Ogawa T. Angew. Chem. Int. Ed. Engl. 1994;33:1765-1767; J. Am. Chem. Soc. 1997;119:5562-5566.
6. [3] Stork, G, Kim GJ. J. Am. Chem. Soc. 1992;114:1087-1088; Bols M. J. Acta Chem. Scand. 1996;50:931-937; Ito Y, Ogawa T. Angew. Chem. Int. Ed. Engl. 1994;33:1765-1767; J. Am. Chem. Soc. 1997;119:5562-5566.
7. [3] Stork, G, Kim GJ. J. Am. Chem. Soc. 1992;114:1087-1088; Bols M. J. Acta Chem. Scand. 1996;50:931-937; Ito Y, Ogawa T. Angew. Chem. Int. Ed. Engl. 1994;33:1765-1767; J. Am. Chem. Soc. 1997;119:5562-5566.
8. [3] Stork, G, Kim GJ. J. Am. Chem. Soc. 1992;114:1087-1088; Bols M. J. Acta Chem. Scand. 1996;50:931-937; Ito Y, Ogawa T. Angew. Chem. Int. Ed. Engl. 1994;33:1765-1767; J. Am. Chem. Soc. 1997;119:5562-5566.
9. [4] Ziegler T, Lau R. Tetrahedron Lett. 1995;36:1417-1420; Schüle G, Ziegler T. Liebigs Ann. 1996;1599-1607.
10. [4] Ziegler T, Lau R. Tetrahedron Lett. 1995;36:1417-1420; Schüle G, Ziegler T. Liebigs Ann. 1996;1599-1607.
11. [5] Valverde S, Gomez AM, Hernandez A, Herradon B, Lopez JC. J. Chem. Soc., Chem. Commun. 1995;2005-2006; Tetrahedron Lett. 1996;37:1105-1108; Yamada H, Imamura K, Takahashi T. Tetrahedron Lett. 1997;38:391-394.
12. [5] Valverde S, Gomez AM, Hernandez A, Herradon B, Lopez JC. J. Chem. Soc., Chem. Commun. 1995;2005-2006; Tetrahedron Lett. 1996;37:1105-1108; Yamada H, Imamura K, Takahashi T. Tetrahedron Lett. 1997;38:391-394.
13. [5] Valverde S, Gomez AM, Hernandez A, Herradon B, Lopez JC. J. Chem. Soc., Chem. Commun. 1995;2005-2006; Tetrahedron Lett. 1996;37:1105-1108; Yamada H, Imamura K, Takahashi T. Tetrahedron Lett. 1997;38:391-394.
14. [6] Schmidt RR, Stumpp M. Liebigs Ann Chem. 1983,1249; Behrendt ME, Schmidt RR. Tetrahedron Lett. 1993;34:6733-6736.
15. [6] Schmidt RR, Stumpp M. Liebigs Ann Chem. 1983,1249; Behrendt ME, Schmidt RR. Tetrahedron Lett. 1993;34:6733-6736.
16. [7] Iimori T, Shibazaki T, Ikegami S. Tetrahedron Lett. 1996;37:2267-2270.
17. [8] Scheffler G, Schmidt RR. Tetrahedron Lett 1997;38:2943-2946; J. Org. Chem., submitted; and references therein.
18. [8] Scheffler G, Schmidt RR. Tetrahedron Lett 1997;38:2943-2946; J. Org. Chem., submitted; and references therein.
19. [9] Mukai C, Itoh T, Hanaoka M. Tetrahedron Lett. 1997;38:4595-4598.
20. [10] Mootoo DR, Konradson P, Udodong U, Fraser-Reid B J. Am. Chem. Soc. 1988;110: 5583-5584.
21. [11] Kiss J, Taschner J. Carbohydr., Nucleosides, Nucleotides 1977;4: 101-119
22. [12] Kochetkov N, Zhulin VM. Carbohydr. Res. 1987;167:C8-C10.
23. [13] Kondo, Y. Agric. Biol. Chem. 1975;39:1879-1881.
24. 13C assignments by DQF-COSY and HMQC spectra: Geyer A, Huchel U, Schmidt RR. Magn. Reson. Chem. submitted.
25. 2Ph).