Synthesis of pyrimidine and purine nucleosides피리미딘 및 퓨린 뉴클레오시드의 합성

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Amino-nucleic acids and amino-heterocycles reacted readily with tbuthylthionitrate or t-buthylthion itrate in the presence of anhydrous sodium tetrafluoroborate in neutral and aprotic media to afford the corresponding fluoronucleic acids and fluoro-heterocycles respectively in good yields. 1-(Tetrahydro-2-furyl) pyrimidine and 9-(tetrahydro-2-furyl) purine derivatives were successfully synthesized in good yields by the reaction of trimethylsilylated pyrimidine and purine bases with 2-acetoxytetrahydrofuran using a new catalyst of cesium chloride in acetonitrile under mild conditions. N3-Methylated purine acyclic nucleosides as analogues of acyclovir were newly synthesized from imidazole precursors so that structureactivity relationships in this area could be explored. 4,5-Dicyanoimidazole was alkylated and then the 5-cyano group was converted to amino group by Hofmann rearrangement reaction to afford the corresponding 1-substituted-5-amino-4-imidazolecarbonitriles as the important precursors for the synthesis of purine nucleosides. Reaction of 6-amino-1,3-dimethyluracil with benzoylisothiocyanate or ethoxycarbonylisothiocyanate afforded the corresponding thioureido derivatives and then subsequently treated with hydroxylamine to afford the 8-aminoxantines respectively. 6-Amono-2-mercaptopurine was silylated, condensed with peracylated sugar and selectively methylated at N1-position to give N1-methyl-2-thioadenosine as a sulfur analogue of doridosine. Electrophilic additions of phenylsulfenyl chloride or phenylselenenyl chloride to a carbon-carbon double bond of c-5,6 region of uracils in the presence of silver reagents directly gave the corresponding 5-phenylsulfydryl-or 5-phenylselenenyl uracils in good yields. The 5-phenylselenenyluracils were investigated for the modification of pyrimidine base through the various transformations due to some unique properties of organic-seleno group.
Advisors
Kim, Yong-Hae김용해
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1991
Identifier
61615/325007 / 000865349
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1991.2, [ xi, 152 p. ]

URI
http://hdl.handle.net/10203/31352
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=61615&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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