86392-75-8Relevant articles and documents
Synthesis of 2-Amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-4H-pyrrolopyrimidin-4-one, a New Isostere of 2'-Deoxyguanosine
Winkeler, Heinz-Dieter,Seela, Frank
, p. 3119 - 3122 (1983)
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A facile and improved synthesis of tubercidin and certain related pyrrolo[2,3-d]pyrimidine nucleosides by the stereospecific sodium salt glycosylation procedure [1]
Ramasamy,Imamura,Robins,Revankar
, p. 1893 - 1898 (2007/10/02)
A simple synthesis of tubercidin, 7-deazaguanosine and 2'-deoxy-7-deazaguanosine has been accomplished using the sodium salt glycosylation procedure. Reaction of the sodium salt of 4-chloro- and 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine, 3 and 4, respectively, with 1-chloro-2,3-O-isopropylidene,5-O-(t-butyl)dimethylsilyl-α-D-ribofur nose gave the corresponding protected nucleosides 6 and 7 with β-anomeric configuration. Deprotection of 6 provided 8, which on heating with methanolic ammonia gave tubercidin in excellent yield. Functional group transformation of 7, followed by deisopropylidenation gave 2-aminotubercidin and 2-amino-7-β-ribofuranosylpyrrolo[2,3-d]pyrimidine-4(3H)-thione. Treatment of 7 with 1N sodium methoxide followed by exposure to aqueous trifluoroacetic acid, and ether cleavage furnished 7-deazaguanosine. 2'-Deoxy-7-deazaguanosine and 2'-deoxy-7-deaza-6-thioguanosine were also prepared by using similar sequence of reactions employing 4 and 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose.
Synthesis of 7-Deaza-2',3'-dideoxyguanosine by Deoxygenation of Its 2'-Deoxy-β-D-ribofuranoside
Seela, Frank,Muth, Heinz-Peter
, p. 215 - 220 (2007/10/02)
7-Deaza-2',3'-dideoxyguanosine (4) was prepared by Barton deoxygenation from 7-deaza-2'-deoxyguanosine (1).Protection of the 5'-hydroxy group was accomplished by the 4,4'-dimethoxytriphenylmethyl residue.The 2-amino function was protected either with the same group or the dimethylaminomethylene residue.Assignment of 1H- and 13C-NMR signals of the 2',3'-dideoxy-β-D-glycero-pentofuranosyl moiety of 4 was made on the basis of 2D-NMR spectra.In contrast to 2',3'-dideoxyguanosine compound 4 has an extremely stable N-glycosylic bond towards proton-catalyzed hydrolysis.