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5'-O-三苯甲基-O2,3'-环脱水胸苷的亲核N1→N3重排

Nucleophilic N1-->N3 rearrangement of 5'-O-trityl-O2,3'-cycloanhydrothymidine.

作者信息

Yang X B, Misiura K, Stec W J, Potrzebowski M J, Kaźmierski S, Wieczorek M, Majzner W R, Bujacz G D

机构信息

Polish Academy of Sciences, Centre of Molecular and Macromolecular Studies, Lódź.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2000 Oct-Dec;19(10-12):1657-73. doi: 10.1080/15257770008045451.

DOI:10.1080/15257770008045451
PMID:11200264
Abstract

5'-O-Trityl-O2,3'-cycloanhydrothymidine (1) heated at 150 degrees C in the presence of O,O-diethyl phosphate or O,O-diethyl phosphorothioate anions undergoes rearrangement into N3-isomer (2); its structure was established by both advanced NMR methods and X-ray crystallographic studies. The most probable mechanism of 1-->2 rearrangement relies upon reversibility of glycosidic bond cleavage process.

摘要

5'-O-三苯甲基-O2,3'-环脱水胸苷(1)在磷酸二乙酯或硫代磷酸二乙酯阴离子存在下于150℃加热,会重排为N3-异构体(2);其结构通过先进的核磁共振方法和X射线晶体学研究得以确定。1→2重排最可能的机制依赖于糖苷键断裂过程的可逆性。

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