Studies on the construction of glycosidic linkage in guanofosfocins. Glycosylation of 8-oxoinosine and 8-oxoguanosine derivatives with mannopyranosyl bromide

Tetrahedron Letters

Volumn 44, Issue 25, 2003, Pages 4729-4732

  Sugimura, Hideyuki ^a   Natsui, Yumiko ^a  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

8 OXOINOSINE; FOSFOMYCIN; GUANOSINE DERIVATIVE; INOSINE DERIVATIVE; MANNOPYRANOSYL BROMIDE; PYRAN DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL MODEL; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLYCOSYLATION; ISOMER; ISOMERISM; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038778524     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01013-X     Document Type: Article

References (11)

1. Katoh, H.; Yamada, M.; Iida, K.; Aoki, M.; Itezono, Y.; Nakayama, M.; Suzuki, Y.; Watanabe, M.; Simada, H.; Fujimari, H.; Nagata, N.; Ohshima, S.; Watanabe, J.; Kamiyama, J. In Abstract of the 38th Symposium of the Chemistry of Natural Products, Sendai, Japan, 1996. (Chem. Abstr. 1996, 125, 322575).
2. Stansfield K., Kanamori H., Sugimura H. New J. Chem. 1999;9.
3. Sugimura H., Stansfield K. Synlett. 1998;985.
4. 13C NMR δ 99.9 from Ref. 1].
5. Freestone A.J., Hough L., Richardson A.C. Carbohydr. Res. 28:1973;378.
6. For instance: (a) Czernecki, S.; Georgoulis, C.; Provelenghiou, C. Tetrahedron Lett. 1976, 17, 3535; (b) Kanai, K.; Sakamoto, S.; Ogawa, S.; Suami, T. Bull. Chem. Soc. Jpn. 1987, 60, 1529; (c) Lipshutz, B. H.; Moretti, R.; Crow, R. Tetrahedron Lett. 1989, 30, 15.
7. For instance: (a) Czernecki, S.; Georgoulis, C.; Provelenghiou, C. Tetrahedron Lett. 1976, 17, 3535; (b) Kanai, K.; Sakamoto, S.; Ogawa, S.; Suami, T. Bull. Chem. Soc. Jpn. 1987, 60, 1529; (c) Lipshutz, B. H.; Moretti, R.; Crow, R. Tetrahedron Lett. 1989, 30, 15.
8. For instance: (a) Czernecki, S.; Georgoulis, C.; Provelenghiou, C. Tetrahedron Lett. 1976, 17, 3535; (b) Kanai, K.; Sakamoto, S.; Ogawa, S.; Suami, T. Bull. Chem. Soc. Jpn. 1987, 60, 1529; (c) Lipshutz, B. H.; Moretti, R.; Crow, R. Tetrahedron Lett. 1989, 30, 15.
9. 4NI was added successively at room temperature. The reaction mixture was stirred at the designated temperature for the stated time, and then filtrated through Celite. The filtrate was evaporated under reduced pressure. The residue was purified by silica gel TLC (hexane-AcOEt) to afford the mannosylated products 3, 4, 6, 7 and 9.
10. 8-Oxopurine nucleosides were prepared according to the procedures described in the following literature: Schulz B.S., Pfleiderer W. Helv. Chim. Acta. 70:1987;210.
11. For a review, see: Paulsen H. Angew. Chem., Int. Ed. Engl. 29:1990;823.