An Efficient One-pot N-Acylation of Deoxy- and Ribo-cytidine Using Carboxylic Acids Activated in situ with 2-Chloro-4,6-dimethoxy-1,3,5-triazine

Rode, Ambadas B.; Son, Sang Jun; Hong, In–Sun

doi:10.5012/bkcs.2010.31.7.2061

Cited by 5 publications

(2 citation statements)

References 21 publications

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“…An efficient one-pot N-acylation of deoxyand ribo-cytidine using carboxylic acids activated in situ with 2-chloro-4,6-dimethoxy-1,3,5-triazine 12 has also been reported (Rode, Son, & Hong, 2010). Diverse carboxylic acids efficiently reacted with pyrimidine and/or purine nucleobases in the presence of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine 13) and NaH/Et 3 N in DMF/MeCN (1:1) affording a facile and selective one-pot N-acylation of nucleobases in good yields (Rad, Behrouz, Asrari, & Khalafi-Nezhad, 2014).…”

Section: Use Of Activated Estersmentioning

confidence: 99%

Nucleobase Protection of Deoxyribo‐ and Ribonucleosides

Meher

Iyer

2017

CP Nucleic Acid Chemistry

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Oligonucleotides carrying a variety of chemical modifications including conjugates are finding increasing applications in therapeutics, diagnostics, functional genomics, proteomics, and as research tools in chemical and molecular biology. The successful synthesis of oligonucleotides primarily depends on the use of appropriately protected nucleoside building blocks including the exocyclic amino groups of the nucleobases, the hydroxyl groups at the 2'-, 3'-, and 5'-positions of the sugar moieties, and the internucleotide phospho-linkage. This unit is a thoroughly revised update of the previously published version and describes the recent development of various protecting groups that facilitate reliable oligonucleotide synthesis. In addition, various protecting groups for the imide/lactam function of thymine/uracil and guanine, respectively, are described to prevent irreversible nucleobase modifications that may occur in the presence of reagents used in oligonucleotide synthesis. © 2017 by John Wiley & Sons, Inc.

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Section: Use Of Activated Estersmentioning

confidence: 99%

Nucleobase Protection of Deoxyribo‐ and Ribonucleosides

Meher

Iyer

2017

CP Nucleic Acid Chemistry

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“…with an acyl chain would generate the solvophobic forces also required for gelation. By adapting previous literature 18 used to synthesise other nucleoside conjugates we were able to selectively acylate the N-position of the nucleobase using a series of fatty acids via a simple one-pot procedure (Figure 1b) generating compounds 2-5. The formation of an activated triazine ester favours the addition on the N-position over the less nucleophilic 5'-position.…”

Section: Introductionmentioning

confidence: 99%