Synthesis of 8-(mannosyloxy)adenosine: A novel nucleoside-carbohydrate hybrid

Synlett

Volumn , Issue 9, 1998, Pages 985-986

  Sugimura, Hideyuki ^a,b   Stansfield, Kevin ^a  

^a NOGUCHI INSTITUTE   (Japan)

^b YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012062323     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1849     Document Type: Article

References (13)

1. Katoh, H.; Yamada, M.; Iida, K.; Aoki, M.; Itezono, Y.; Nakayama, N.; Suzuki, Y.; Watanabe, M.; Shimada, H.; Fujimari, H.; Nagata, N.; Ohshima, S.; Watanabe, J.; Kamiyama J. In Abstract of the 38th Symposium on the Chemistry of Natural Products, Sendai, Japan, 1996: p 115.
2. (Chem. Abstr., 1996, 125, 322575)
3. Generally, 8-oxoadenosine is prepared by the procedures described in the following literatures: (a) Holmes, R. E.; Robins, R. K. J. Am. Chem. Soc. 1965, 87, 1772.
4. (b) Buenger, G. S.; Nair, V. Synthesis 1990, 962.
5. Stansfield, K.; Kanamori, H.; Sugimura, H. the manuscript is submitted to J. Chem. Soc., Chem. Commun.
6. For a review, Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
7. Nicolaou, K. C.; Seitz, S. P.; Papahatjis, D. P. J. Am. Chem. Soc. 1983, 105, 2430.
8. Schulz, B. S.; Pfleiderer, W. Helv. Chim. Acta 1987, 70, 210.
9. 3-Methoxy-2-pyridyl glycosides have also been prepared from silver 3-methoxy-2-pyridoxide and peracylated glycosyl bromides in refluxing toluene. See, Lou, B.; Reddy, G. V.; Wang H.; Hanessian, S. In "Preparative Carbohydrate Chemistry", Hanessian S. ed.; Marcel Dekker, Inc.: New York, 1997: p 389.
10. 13C NMR δ 25.3, 27.1, 64.6, 68.6, 71.1, 72.5, 72.7, 73.3, 73.7, 74.0, 74.7, 75.3, 77.2, 78.9, 82.4, 83.1, 86.5, 87.0, 88.1, 98.0, 113.6, 116.8, 126.9, 127.5, 127.6, 127.7, 127.8, 127.9, 128.1, 128.3, 128.4, 128.5, 128.7, 128.8, 129.0, 137.8, 137.9, 138.1, 138.2, 143.8, 145.3, 147.4, 150.2, 151.7, 152.0.
11. Maki, Y.; Kameyama, K.; Suzuki, M.; Sako, M.; Hirota, K. J. Chem. Res. (M) 1984, 3601.
12. Beaucage, S. L.; Iyer, R. P. Tetrahedron, 1992, 48, 2223.
13. Bock, K.; Pedersen C. Adv. Carbohydr. Chem. Biochem., 1983, 41, 27.