N (3)??Protection of Thymidine with Boc for an Easy Synthetic Access to Sugar??Alkylated Nucleoside Analogs

…, L De Napoli, D Montesarchio

Index: Simeone, Luca; De Napoli, Lorenzo; Montesarchio, Daniela Chemistry and Biodiversity, 2012 , vol. 9, # 3 p. 589 - 597

Full Text: HTML

Citation Number: 4

Abstract

Abstract The use of Boc as a nucleobase-protecting group in the synthesis of sugar-modified thymidine analogs is reported. Boc was easily inserted at N (3) by a simple and high- yielding reaction and found to be stable to standard treatments for the removal of Ac and t BuMe 2 Si (TBDMS) groups, as well as to ZnBr 2-mediated 4, 4′-dimethoxytrityl (DMTr) deprotection. Boc Protection proved to be completely resistant to the strong basic ...

Related Articles:

Efficient synthesis of nucleoside diphosphate glycopyranoses

[Wendicke, Silke; Warnecke, Svenja; Meier, Chris Angewandte Chemie - International Edition, 2008 , vol. 47, # 8 p. 1500 - 1502]

A Versatile Synthesis of 5′??Functionalized Nucleosides Through Regioselective Enzymatic Hydrolysis of Their Peracetylated Precursors

[Bavaro, Teodora; Rocchietti, Silvia; Ubiali; Filice, Marco; Terreni, Marco; Pregnolato, Massimo European Journal of Organic Chemistry, 2009 , # 12 p. 1967 - 1975]

Exploring the potential of 3′-O-carboxy esters of thymidine as inhibitors of ribonuclease A and angiogenin

[Ghosh, Kalyan S.; Debnath, Joy; Dutta, Palash; Sahoo, Bijaya K.; Dasgupta, Swagata Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 6 p. 2819 - 2828]

Conformational transmission in nucleotides containing trigonal bipyramidal phosphorus as the internucleoside linkage

[Koole, Leo H.; Genderen, Marcel H. P. van; Buck, Henk M. Journal of Organic Chemistry, 1988 , vol. 53, # 22 p. 5266 - 5272]

Further optimization of detritylation in solid-phase oligodeoxyribonucleotide synthesis

[Tram, Kha; Sanghvi, Yogesh S.; Yan, Hongbin Nucleosides, Nucleotides and Nucleic Acids, 2011 , vol. 30, # 1 p. 12 - 19]

More Articles...