207448-92-8Relevant articles and documents
Synthesis and Separation of Diastereomers of Ribonucleoside 5′-(α-P-Borano)triphosphates
He, Kaizhang,Hasan, Ahmad,Krzyzanowska, Bozenna,Shaw, Barbara Ramsay
, p. 5769 - 5773 (1998)
Nucleoside boranophosphates, in which one of the phosphate oxygens is replaced by a borane group, are isoionic and isoelectronic analogues of naturally occurring nucleotides. Boranophosphates also are biochemically important congeners of phosphorothioates and methylphosphonates. We have developed a convenient one-pot method to synthesize the set of ribonucleoside (A, U, G, and C) 5′-(α-P-borano)triphosphates. Phosphitylation of the 2′,3′-protected ribonucleoside with 2-chloro4H-1,3,2-benzodioxaphosphorin-4-one gives the 5′-phosphite intermediate 2 which undergoes in situ substitution in the presence of pyrophosphate to give the cyclic intermediate, P2,P3-dioxo-P1-ribonucleosidylcyclotriphosphate 3. Immediate oxidation of compound 3 with amine·borane complex results in ribonucleoside 5′-(α-P-borano)cyclotriphosphate 4. Subsequent reaction of compound 4 with water followed by ammonium hydroxide yields the crude product as a diastereomeric mixture of ribonucleoside 5′-(α-P-borano)triphosphate 6. Pure compound 6 is isolated in 30-45% overall yield using ion-exchange chromatography. The separation of two diastereomers of ribonucleoside 5′-(α-P-borano)triphosphate 6 is achieved by reverse phase HPLC.
Synthesis of α-P-modified nucleoside diphosphates with ethylenediamine
Li, Ping,Xu, Zhihong,Liu, Hongyan,Wennefors, Charlotta K.,Dobrikov, Mikhail I.,Ludwig, Janos,Shaw, Barbara Ramsay
, p. 16782 - 16783 (2005)
This report describes a one-pot synthesis of α-P-borano-, α-P-thio-, and α-P-seleno-modified nucleoside diphosphate analogues that are otherwise difficult to obtain. The key step involves the intramolecular nucleophilic attack by an amino group in 5 to re
