A mild and rapid glycosylation reaction between pyrimidine bases and 2-deoxyribofuranosyl N,N,N',N'-tetramethylphosphoroamidates

Heterocycles

Volumn 42, Issue 2, 1996, Pages 485-488

  Iimori, Takamasa ^a   Kobayashi, Hiroshi ^a   Hashimoto, Shun Ichi ^a,b   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0142142314     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s71     Document Type: Article

References (16)

1. H. Vorbrüggen, K. Krolikiewicz, and B. Bennua, Chem. Ber., 1981, 114, 1234 .
2. N2 type displacement using α-anomers of the chlorosugars affords β-nucleosides selectively: H. Aoyama, Bull. Chem. Soc. Jpn., 1987, 60, 2073; Z. Kazimierczuk, H. B. Cottam, G. R. Revankar, and R. K. Robins, J. Am. Chem. Soc., 1984, 106, 6379.
3. N2 type displacement using α-anomers of the chlorosugars affords β-nucleosides selectively: H. Aoyama, Bull. Chem. Soc. Jpn., 1987, 60, 2073; Z. Kazimierczuk, H. B. Cottam, G. R. Revankar, and R. K. Robins, J. Am. Chem. Soc., 1984, 106, 6379.
4. M. E. Jung and C. Castro, J. Org. Chem., 1993, 58, 807; K. Sujino and H. Sugimura, Chem. Lett., 1993, 1187.
5. M. E. Jung and C. Castro, J. Org. Chem., 1993, 58, 807; K. Sujino and H. Sugimura, Chem. Lett., 1993, 1187.
6. S. Hashimoto, T. Honda, and S. Ikegami, J. Chem. Soc., Chem. Commun., 1989, 685; S. Hashimoto, T. Honda, and S. Ikegami, Heterocycles, 1990, 30, 775; S. Hashimoto, T. Honda, and S. Ikegami, Chem. Pharm. Bull., 1990, 38, 2323; S. Hashimoto, T. Honda, and S. Ikegami, Tetrahedron Lett., 1990, 31, 4769; S. Hashimoto, T. Honda, and S. Ikegami, Tetrahedron Lett., 1991, 32, 1653.
7. S. Hashimoto, T. Honda, and S. Ikegami, J. Chem. Soc., Chem. Commun., 1989, 685; S. Hashimoto, T. Honda, and S. Ikegami, Heterocycles, 1990, 30, 775; S. Hashimoto, T. Honda, and S. Ikegami, Chem. Pharm. Bull., 1990, 38, 2323; S. Hashimoto, T. Honda, and S. Ikegami, Tetrahedron Lett., 1990, 31, 4769; S. Hashimoto, T. Honda, and S. Ikegami, Tetrahedron Lett., 1991, 32, 1653.
8. S. Hashimoto, T. Honda, and S. Ikegami, J. Chem. Soc., Chem. Commun., 1989, 685; S. Hashimoto, T. Honda, and S. Ikegami, Heterocycles, 1990, 30, 775; S. Hashimoto, T. Honda, and S. Ikegami, Chem. Pharm. Bull., 1990, 38, 2323; S. Hashimoto, T. Honda, and S. Ikegami, Tetrahedron Lett., 1990, 31, 4769; S. Hashimoto, T. Honda, and S. Ikegami, Tetrahedron Lett., 1991, 32, 1653.
9. S. Hashimoto, T. Honda, and S. Ikegami, J. Chem. Soc., Chem. Commun., 1989, 685; S. Hashimoto, T. Honda, and S. Ikegami, Heterocycles, 1990, 30, 775; S. Hashimoto, T. Honda, and S. Ikegami, Chem. Pharm. Bull., 1990, 38, 2323; S. Hashimoto, T. Honda, and S. Ikegami, Tetrahedron Lett., 1990, 31, 4769; S. Hashimoto, T. Honda, and S. Ikegami, Tetrahedron Lett., 1991, 32, 1653.
10. S. Hashimoto, T. Honda, and S. Ikegami, J. Chem. Soc., Chem. Commun., 1989, 685; S. Hashimoto, T. Honda, and S. Ikegami, Heterocycles, 1990, 30, 775; S. Hashimoto, T. Honda, and S. Ikegami, Chem. Pharm. Bull., 1990, 38, 2323; S. Hashimoto, T. Honda, and S. Ikegami, Tetrahedron Lett., 1990, 31, 4769; S. Hashimoto, T. Honda, and S. Ikegami, Tetrahedron Lett., 1991, 32, 1653.
11. S. Hashimoto, Y. Yanagiya, T. Honda, H. Harada, and S. Ikegami, Tetrahedron Lett., 1992, 33, 3523.
12. 5 was found to be difficult because of their high reactivity. Benzyl-protected ribofuranosyl N,N,N',N'-tetramethylphosphoroamidate was also unstable and considerable decomposition occurred during chromatographic purification.
13. 2 as promoteres improved β-selectivity slightly (β / α = 2.1), but yields were considerably low (10 - 20%). It was also found that the use of excess of TMSOTf (5 equiv.) afforded the β-anomer predominantly (β / α = 5.3) in 10% yield. These results might be ascribed to the selective decomposition of the reaction intermediate such as i (β-ion pair) which afforded the α-anomer by the backside attack of nucleoside base (B). Chemical equations presented.
14. K. Wiesner, T. Y. R. Tsai, and H. Jin, Helv. Chim. Acta, 1985, 68, 300.
15. H. Sugimura, K. Sujino, and K. Osumi, Tetrahedron Lett., 1992, 33, 2515.
16. Kawakami and co-workers have been reported that a large amount of silylated base was required to obtain high stereoselectivity in their synthesis of 2′-deoxy-5-trifluoromethyluridine: Kawakami, T. Ebata, K. Koseki, H. Matsushita, Y, Naoi, K. Ito, and N. Mizutani, Heterocycles, 1990, 31, 569.