A Study on Synthesis and Upscaling of 2′-O-AECM-5-methyl Pyrimidine Phosphoramidites for Oligonucleotide Synthesis

Autor:	Kristina Karalė, Martin Bollmark, Rouven Stulz, Dmytro Honcharenko, Ulf Tedebark, Roger Strömberg
Jazyk:	angličtina
Rok vydání:	2021
Předmět:	2′-O-(N-(aminoethyl)carbamoyl)methyl modification phase transfer catalysis (PTC) 5-methyluridine 5-methylcytidine oligonucleotides alkylation Organic chemistry QD241-441
Zdroj:	Molecules, Vol 26, Iss 22, p 6927 (2021)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules26226927
Popis:	2′-O-(N-(Aminoethyl)carbamoyl)methyl-modified 5-methyluridine (AECM-MeU) and 5-methylcytidine (AECM-MeC) phosphoramidites are reported for the first time and prepared in multigram quantities. The syntheses of AECM-MeU and AECM-MeC nucleosides are designed for larger scales (approx. 20 g up until phosphoramidite preparation steps) using low-cost reagents and minimizing chromatographic purifications. Several steps were screened for best conditions, focusing on the most crucial steps such as N3 and/or 2′-OH alkylations, which were improved for larger scale synthesis using phase transfer catalysis (PTC). Moreover, the need of chromatographic purifications was substantially reduced by employing one-pot synthesis and improved work-up strategies.
Databáze:	Directory of Open Access Journals
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