Synthesis of a Novel, Optically Active Uridine Analog Containing a 1,4-Dioxane Sugar Moiety. Synthesis of the Corresponding Dinucleotide

REFERENCES

• Ichikawa , Eiko and Kato , Kuniki . 2001 . Sugar-modified nucleosides in past 10 years, a review . Current Medicinal Chemistry , 8 : 385 – 423 .
   PubMed Web of Science ®Google Scholar
• Grate , J. W. and Frye , G. C. 1966 . Sensors Update , Edited by: Baltes , H. , Göpel , W. and Hesse , J. vol. 2 , 10 – 20 . Weinheim : Wiley-VCH .
   Google Scholar
• Szarek , W. A. , Pinto , B. M. and Iwakawa , M. 1985 . Synthesis and biological activity of nucleoside analogues involving modifications in the carbohydrate ring . Can. J. Chem. , 63 : 2149 – 2161 .
   Google Scholar
• Hronowski , L. J. and Szarek , W. A. 1982 . Synthesis and biological evaluation of novel pyrimidine nucleoside analogues of 1,4-oxathiane, 1,4-dithiane, and 1,4-dioxane . J. Med. Chem. , 25 : 522 – 526 .
   PubMedGoogle Scholar
• Prisbe , E. J. 1986 . Synthesis and antiviral evaluation of 1,4-dioxane nucleoside analogueues related to nucleoside dialdehydes . J. Med. Chem. , 29 : 2445 – 2450 .
   PubMedGoogle Scholar
• Mitsuaki , M. , Naoko , K. , Yamaizumi , Z. , Okamoto , Y. , Nagahara , K. and Takayanagi , H. 1997 . Synthesis of a novel dioxane nucleoside having two bases, 2(R)-(5-fluorouracil-1-yl)-5(R)-hydroxymethyl-3(R)-(uracil-1-yl)-1,4-dioxane and its 2(S)-isomer, from uridine . Tetrahedron Lett. , 38 : 6841 – 6844 .
   Google Scholar
• Szarek , W. A. , Vyas , D. M. and Achmatowicz , B. 1975 . Synthesis of nucleoside analogues of 1,4-oxathiane, 1,4-dothiane, and 1,4-dioxane . J. Heterocycle. Chem. , 12 : 123 – 127 .
   Google Scholar
• Van Aerschot , A. , Balzarini , J. , De Clercq , E. and Herdewijn , P. 1991 . Synthesis and antiviral activity of 1,4-dioxane, 1,4-oxathiane and morpholine nucleoside analogs . Nucleosides Nucleotides , 10 : 591 – 592 .
   Web of Science ®Google Scholar
• Van Aerschot , A. , Janssen , G. and Herdewijn , P. 1990 . Nucleoside analogs with a 1,4-dioxane, 1,4-oxathiane or 1,4-oxazine ring structure as the carbohydrate fragment . Bulletin des Societes Chimiques Belges , 99 : 769 – 777 .
   Google Scholar
• Sinha , N. D. , Biernat , J. , Mcmanus , J. and Köster , H. 1984 . Polymer support oligonucleotide synthesis. XVIII: Use of -cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product . Nucleic Acids Res , 12 : 4539 – 4557 .
   PubMed Web of Science ®Google Scholar
• Baskaran , S. , Aurich , H. G. , Biesemeier , F. and Harms , K. 1998 . Cycloadducts from highly functionalized nitrones and oximes as ligands in the enantioselective addition of diethylzinc to benzaldehyde . J. Chem. Soc., Perkin Trans. 1 , 22 : 3717 – 3724 .
   Google Scholar
• Nagashima , N and Ohno , M. 1991 . Selective monoalkylation of acyclic diols by means of dibutyltin oxide and fluoride salts . Chem. Pharm. Bull. , 39 : 1972 – 1982 .
   Google Scholar
• Nagashima , N. and Ohno , M. 1987 . An efficient O-monoalkylation of dimethyl L-tartrate via O-stannylene acetal with alkyl halides in the presence of cesium fluoride . Chem. Lett. , 1 : 141 – 144 .
   Google Scholar
• Marshall , J. A. , Andersen , N. H. and Hochstetler , A. R. 1967 . Reduction of malonic enolates with lithium aluminum hydride . J. Org. Chem. , 32 : 113 – 118 .
   Web of Science ®Google Scholar
• Shi , M. , Jiang , J. and Feng , Y. 2000 . Chiral C2 -symmetric 2,3-disubstituted aziridine and 2,6-disubstituted piperidine as chiral ligands in the addition reaction of diethylzinc with arylaldehydes . Tetrahedron: Asymmetry , 11 : 4923 – 4933 .
   Google Scholar
• Marshall , J. A. and Beaudion , S. 1994 . Stereoselective Synthesis of Higher Sugars by Homologation of Carbohydrate-Derived Enals with Nonracemic-(Silyloxy) Allylic Stannanes and Substrate-Directed Hydroxylation . J. Org. Chem. , 59 : 6614 – 6619 .
   Google Scholar
• Albizati , K. F. and Babu , S. 2001 . A synthesis of the HIV-protease inhibitor nelfinavir from D-tartaric acid . Tetrahedron Lett. , 42 : 6481 – 6485 . etc.
   Web of Science ®Google Scholar
• Takano , S. , Kurotaki , A. , Sekiguchi , Y. , Satoh , S. , Hirama , M. and Ogasawara , K. 1986 . Selective manipulation of hydroxy groups in (2S,3S)-threitol . Synthesis , 10 : 811 – 817 .
   Google Scholar
• Vorbrüggen , H. and Krolikiewicz , K. 1981 . Nucleoside syntheses. XXII. Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts . Chem. Ber. , 114 : 1234 – 1255 .
   Google Scholar
• Vorbrüggen , H. and Höfle , G. 1981 . Nucleoside syntheses. XXIII. On the mechanism of nucleoside synthesis . Chem. Ber. , 114 : 1256 – 1268 .
   Google Scholar
• Colacino , E. , Sindona , G. , Gosselin , G. and Mathé , C. 2003 . Synthesis and Biological Evaluation of Some 5-Nitro- and 5-Amino Derivatives of 2′-Deoxycytidine, 2′,3′-Dideoxyuridine, and 2′,3′-Dideoxycytidine . Nucleosides, Nucleotides Nucleic Acids , 22 : 2013 – 2026 .
   PubMed Web of Science ®Google Scholar
• Fisher , E. F. and Caruthers , M. H. 1983 . Color coded triarylmethyl protecting groups useful for deoxypolynucleotide synthesis . Nucleic Acids Res. , 11 : 1589 – 1599 .
   PubMedGoogle Scholar
• Stütz , J. A.R. and Richert , C. 2004 . Synthesis of a formamidine-protected 5′-amino-2′,5′-dideoxyguanosine phosphoramidite and preparation of 5′-acylamidooligonucleotides . Tetrahedron Lett. , 45 : 509 – 513 .
   Google Scholar
• Eisenfuhr , A. and Arora , P. S. 2003 . A ribozyme with michaelase activity: synthesis of the substrate precursors . Bioorg. Med. Chem. , 11 : 235 – 249 .
   PubMedGoogle Scholar
• Ferris , J. P. and Peyser , J. R. 1994 . Rapid and efficient syntheses of phosphorylated dinucleotides . Nucleosides Nucleotides , 13 : 1087 – 1111 .
   PubMedGoogle Scholar
• Gait , M. J. 1984 . Oligonucleotide Synthesis, A Practical Approach , Oxford, Washington, DC : IRL PRESS .
   Google Scholar
• Yu , Q. , Kaffarnik , S. and Carlsen , P. 2008 . Synthesis of Optically Active 1,4-Dioxane Nucleotide Analogues . Synth. Commun. , 38 : 4250 – 4264 .
   Web of Science ®Google Scholar