Synthesis of 2',3',6'-trideoxy-β-D-erythro-hexopyranosyl nucleosides employing intramolecular glycosylation as a key step

Nucleosides and Nucleotides

Volumn 17, Issue 1-3, 1998, Pages 53-63

  Sugimura, Hideyuki ^a   Sujino, Keiko ^a  

^a NOGUCHI INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2',3',6' TRIDEOXY BETA D ERYTHROHEXOPYRANOSYL NUCLEOSIDE; AMICETIN; PYRIMIDINE NUCLEOSIDE; UNCLASSIFIED DRUG;

ARTICLE; GLYCOSYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0031912388     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319808005157     Document Type: Article

References (15)

1. For a review, Lerner, L. M. Chem. Nucleosides Nucleotides 1991, 2, 27-79.
2. For recent studies, (a) Itoh, J.; Miyadoh, S. J. Antibiotics 1992, 45, 846-853 and references cited therein, (b) Shiomi, K.; Haneda, K.; Tomoda, H.; Iwai, Y.; Omura, S. J. Antibiotics 1994, 47, 782-786.
3. For recent studies, (a) Itoh, J.; Miyadoh, S. J. Antibiotics 1992, 45, 846-853 and references cited therein, (b) Shiomi, K.; Haneda, K.; Tomoda, H.; Iwai, Y.; Omura, S. J. Antibiotics 1994, 47, 782-786.
4. Stevens, C. L.; Nielsen, N. A.; Blumbergs, F.; Taylor, K. G. J. Am. Chem. Soc. 1964, 86, 5695-5697.
5. Böhringer, M.; Roth, H.-J.; Hunziker, J.; Göbel, M.; Krishnan, R.; Giger, A.; Schweizer, B.; Schreiber, J.; Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1992, 75, 1416-1477.
6. (a) Sujino, K.; Sugimura, H. Chem. Lett. 1993, 1187-1190.
7. (b) Sujino, K.; Sugimura, H. Tetrahedron Lett. 1994, 35, 1883-1886.
8. (c) Sugimura, H.; Motegi, M.; Sujino, K. Nucleosides Nucleotides 1995, 14, 413-416.
9. Ferrier, R. J.; Prasad, N. J. Chem. Soc. (C) 1969, 570-575.
10. Nicolaou, K. C.; Seitz, S. P.; Papahatjis, D. P. J. Am. Chem. Soc. 1983, 105, 2430-2434.
11. Johansson, R.; Samuelsson, B. J. Chem. Soc., Perkin Trans. I 1984, 2371-2374.
12. Katritzky, A. R.; Baykut, G.; Rachwal, S.; Szafran, M.; Caster, K. C.; Eyler, J. J. Chem. Soc., Perkin Trans. II 1989, 1499-1506.
13. Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc. Perkin Trans. I 1983, 1315-1318.
14. Albert, R.; Dax, K.; Pleschko, R.; Stütz, A. E. Carbohydr. Res. 1985, 137, 282-290.
15. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885-888.