Highly stereoselective synthesis of C-vinyl furanosides through acid-catalyzed SN2 inversion at the C-3 position of 1,2-dideoxy-hept-1-enitols

Carbohydrate Research

Volumn 343, Issue 17, 2008, Pages 2985-2988

  Tsuchiya, Hitoshi ^a   Asakura, Noriaki ^a   Ikeda, Yasunori ^a   Yamada, Hidetoshi ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

1,2 Dideoxy hept 1 enitols; C Vinyl furanosides; Diphenylammonium trifluoromethanesulfonate; SN2 intramolecular debenzyloxyation cycloetherification

Indexed keywords

1,2-DIDEOXY-HEPT-1-ENITOLS; C-VINYL FURANOSIDES; DIPHENYLAMMONIUM TRIFLUOROMETHANESULFONATE; SN2 INTRAMOLECULAR DEBENZYLOXYATION-CYCLOETHERIFICATION;

ACIDS; STEREOCHEMISTRY;

STEREOSELECTIVITY;

1,2 DIDEOXY HEPT 1 ENITOL DERIVATIVE; 2,5 ANHYDRO 3,4,6 TRI O BENZYL DEXTRO TALOSE; 3,6 ANHYDRO 1,2 DIDEOXY HEPT 1 ENITOL DERIVATIVE; 3,6 ANHYDRO 4,5,7 TRI O BENZYL 1,2 DIDEOXY DEXTRO GLUCO HEPT 1 ENITOL; 3,6 ANHYDRO 4,5,7 TRI O BENZYL 1,2 DIDEOXY DEXTRO MANNO HEPT 1 ENITOL; 3,6 ANHYDRO 4,5,7 TRI O BENZYL 1,2 DIDEOXY DEXTRO TALO HEPT 1 ENITOL; 3,6 ANHYDRO 5 O BENZYL 1,2 DIDEOXY DEXTRO MANNO HEPT 1 ENITOL; CARBOHYDRATE DERIVATIVE; DIPHENYLAMMONIUM TRIFLUOROMETHANESULFONATE; FURANOSIDE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ETHERIFICATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

CARBOHYDRATE CONFORMATION; CATALYSIS; IMINO FURANOSES; INDICATORS AND REAGENTS; MODELS, MOLECULAR; STEREOISOMERISM; SUGAR ALCOHOLS; THERMODYNAMICS; VINYL COMPOUNDS;

EID: 53849085455     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2008.08.017     Document Type: Article

References (22)

1. Pankiewicz K.W. Curr. Med. Chem. 6 (1999) 514-634
2. Townsen L.B. Chemistry of Nucleosides and Nucleotides (1988), Plenum, New York
3. Hanessian S., Marcotte S., Machaalani R., Huang G., Pierron J., and Loiseleur O. Tetrahedron 62 (2006) 5201-5214
4. Sisu E., Sollogoub M., Mallet J.-M., and Sinaÿ P. Tetrahedron 58 (2002) 10189-10196
5. Molander G.A., and Haas J. Tetrahedron 55 (1999) 617-624
6. Oikawa Y., Nishi T., and Yonemitsu O. J. Chem. Soc., Perkin Trans. 1 (1985) 7-17
7. Martin O.R., Yang F., and Xie F. Tetrahedron Lett. 36 (1995) 47-50
8. Yang B.-H., Jiang J.-Q., Ma K., and Wu H.-M. Tetrahedron Lett. 36 (1995) 2831-2834
9. Cribiú R., and Cumpstey I. Chem. Commun. (Cambridge) (2008) 1246-1248
10. Wolfe J.P., and Hay M.B. Tetrahedron 63 (2007) 261-290
11. Sharma G.V.M., Chander A.S., Krishnudu K., and Krishna P.R. Tretahedron Lett. 39 (1998) 6957-6960
12. Oka T., Fujiwara K., and Murai A. Tetrahedron 52 (1996) 12091-12110
13. Dehmlow H., Mulzer J., Seilz C., Strecker A.R., and Kohlmann A. Tetrahedron Lett. 33 (1992) 3607-3610
14. Rychnovsky S.D., and Bartlett P.A. J. Am. Chem. Soc. 103 (1981) 3963-3964
15. Yamada H., Nagao K., Dokei K., Kasai Y., and Michihata N. J. Am. Chem. Soc. 130 (2008) 7566-7567
16. Ikeda Y., Nagao K., Tanigakiuchi K., Tokumaru G., Tsuchiya H., and Yamada H. Tetrahedron Lett. 45 (2004) 487-489
17. Wakasugi K., Misaki T., Yamada K., and Tanabe Y. Tetrahedron Lett. 41 (2000) 5249-5252
18. Lancelin J.-M., Pougny J.-R., and Sinaÿ P. Carbohydr. Res. 136 (1985) 369-374
19. Pougny J.-R., Nassr M.A.M., and Sinaÿ P. J. Chem. Soc., Chem. Commun. (1981) 375-376
20. Persky R., and Albeck A. J. Org. Chem. 65 (2000) 5632-5638
21. Martin O.R., Saavedra O.M., Xie F., Liu L., Picasso S., Vogel P., Kizu H., and Asano N. Bioorg. Med. Chem. 9 (2001) 1269-1278
22. Battelli E., D'Andrea P., Mascanzoni S., Passacantilli P., and Piancatelli G. Carbohydr. Res. 306 (1998) 221-230