References
- Tanaka , H. , Hayakawa , H. and Miyasaka , T. 1982 . Tetrahedron , 38 : 2635
- Tanaka , H. , Hayakawa , H. and Miyasaka , T. 1981 . Chem. Pharm. Bull. , 29 : 3565
- Hayakawa , H. , Tanaka , H. and Miyasaka , T. 1985 . Tetrahedron , 41 : 1675 An improved method for the preparation of 1 has been reported:
- Tanaka , H. , Hayakawa , H. and Miyasaka , T. unpublished result
- Hirota , K. , Kanabe , Y. , Kitade , Y. and Maki , Y. 1988 . Nucleic Acids Symposium Series , 20 : 31
- Hayakawa , H. , Tanaka , H. , Maruyama , Y. and Miyasaka , T. 1985 . Chem. Lett. , : 1401 Efficiency and regioselectivity of the LDA lithiation of 3 have been reported:
- Winkley , M. W. and Robins , R. K. J. Org. Chem. , 33 2822 Although condensation of 6-substituted pyrimidines with an appropriately protected sugar derivatives almost always resulted in predominant formation of N3-ribosylated products, improved condensation methods for the preparation of 6-methyluridine have been reported: (1968); R. S. Klein and J. J. Fox, ibid., 37, 4381 (1972); U. Niedballa and H. Vorbrüggen, ibid., 39, 3660 (1974)
- Holý , A. 1974 . Collect. Czech. Chem. Commun. , 39 : 3374 Synthesis of 6-methyluridine from a pentose 2-amino-1′,2′-oxazoline derivative has been reported:
- Slocum , D. W. and Gierer , P. L. 1976 . J. Org. Chem. , 41 : 3668 Tosyl chloride has been used for the reaction with organolithiums:, H. Hayakawa, H. Tanaka, K. Haraguchi, M. Mayumi, M. Nakajima, T. Sakamaki, and T. Miyasaka, Nucleosides and Nucleotides, 7, 121 (1988)
- Pichat , L. and Chatelain , G. 1970 . Bull. Chim. Soc. Fr. , : 1833 Condensation of 6-chloro-2,4-bis-O-trimethylsilyluracil with 2,3,5-tri-O-benzoylribofuranosyl chloride results in the sole formation of N3-ribosylated product:
- Tanaka , H. , Matsuda , A. , Iijima , S. , Hayakawa , H. and Miyasaka , T. 1983 . Chem. Pharm. Bull. , 31 : 2164
- The reaction time can be reduced to 4 h by using dioxane as a solvent, but the yield of 8 was moderate (52%)
- Tamao , K. , Sumitani , K. , Kiso , Y. , Zembayashi , M. , Fujioka , A. , Kodama , S. , Nakajima , I. , Minato , A. and Kumada , M. 1976 . Bull. Chem. Soc. Jpn. , 49 : 1958
- The yields of 4 and 8 were 38 and 31%, respectively. When 4 was treated with 5. 0 equiv of MeMgBr in dioxane for 2 h, a complex mixture of highly polar products resulted along with a 37% yield of 8.
- Though this particular reaction was carried out with 10 equiv of SnMe4, the use of 3. 0 equiv effects almost complete conversion under these conditions; only partial conversion to 8 (16%) was observed by using 1. 2 equiv of SnMe4.
- Crisp , G. T. and Macolino , V. 1990 . Synth. Commun. , 20 : 413 The palladium-catalyzed cross-coupling between aryl-trimethylstannanes and 5-iodouridines has been reported:
- Crisp , G. T. and Flynn , B. L. 1990 . Tetrahedron Lett. , 31 : 1347 Organostannanes have been used for the coupling reaction with 2′,3′,5′-tri-O-acetyl-5-trifluoromethanesulfonyloxyuridine:
- Peters , D. , Hörnfeldt , A.-B. and Gronowitz , S. 1990 . J. Heterocyclic Chem. , 27 : 2165 Quite recently reactions between 5-halogenouracils and aryltributylstannanes were used for the preparation of 5-aryluracil derivatives:
- Satoh , K. , Tanaka , H. , Andoh , A. and Miyasaka , T. 1986 . Nucleosides and Nucleotides , 5 : 461