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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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.
LIQUID-LIQUID AND SOLID-LIQUID PHASE-TRANSFER GLYCOSYLATION OF PYRROLOPYRIMIDINES : STEREOSPECIFIC SYNTHESIS OF 2-DEOXY-β-D-RIBOFURANOSIDES RELATED TO 2'-DEOXY-7-CARBAGUANOSINE
Seela, Frank,Westermann, Bernhard,Bindig, Uwe
, p. 697 - 702 (2007/10/02)
The yield of phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolopyrimidine (3b) with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (4) is limited under liquid-liquid conditions (50percent aq.NaOH, CH2Cl2, Bu4NHSO4) due t