C-glycosidation of unprotected D-glycals with trimethylsilyl cyanide

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1729-1730

  Hayashi, Masahiko ^a   Kawabata, Hirotoshi ^a   Arikita, Osamu ^a  

^a YAMAGUCHI UNIVERSITY   (Japan)

Author keywords

Cyanides; Glycals; Glycosidation; Palladium and compounds

Indexed keywords

CYANIDE; HYDROGEN CYANIDE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033605397     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00038-6     Document Type: Article

References (11)

1. [1] Levy DE, Tang C, "The Chemistry of C-Glycosides", Pergamon. Chapt.2, 1995.
2. [2] De las Heras FG, San Felix A, F-Resa P. Tetrahedton 1983; 39: 1617-1620. Drew KN, Gross PH. J. Org. Chem. 1991; 56:509-513. Raadt A, Griengl H, Klempier N, Stütz AE, J. Org. Chem, 1993; 58:3179-3184, and references cited therein.
3. [2] De las Heras FG, San Felix A, F-Resa P. Tetrahedton 1983; 39: 1617-1620. Drew KN, Gross PH. J. Org. Chem. 1991; 56:509-513. Raadt A, Griengl H, Klempier N, Stütz AE, J. Org. Chem, 1993; 58:3179-3184, and references cited therein.
4. [2] De las Heras FG, San Felix A, F-Resa P. Tetrahedton 1983; 39: 1617-1620. Drew KN, Gross PH. J. Org. Chem. 1991; 56:509-513. Raadt A, Griengl H, Klempier N, Stütz AE, J. Org. Chem, 1993; 58:3179-3184, and references cited therein.
5. 3SiOTf). Toshima K, Ishizuka T, Matsuo G, Nakata M, Tetrahedron Lett. 1994; 35, 5673-5676.
6. 3SiOTf). Toshima K, Ishizuka T, Matsuo G, Nakata M, Tetrahedron Lett. 1994; 35, 5673-5676.
7. 2O) was not always successful, because the addition of methanol to the cyano group giving the corresponding imidate occurred. See, Somasák L. Carbohydr. Res. 1996; 286:167-171. Poonian MS, Nowoswiat EF, J. Org. Chem. 1980; 45: 203-208, and references cited therein.
8. 2O) was not always successful, because the addition of methanol to the cyano group giving the corresponding imidate occurred. See, Somasák L. Carbohydr. Res. 1996; 286:167-171. Poonian MS, Nowoswiat EF, J. Org. Chem. 1980; 45: 203-208, and references cited therein.
9. 3).
10. 4 did not work as a catalyst.
11. [7] Hayashi M, Amano K, Tsukada K, Lamberth C, submitted for publication.