Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides

Autor:	Quanlai Song, Wayne Lloyd, Colin B. Reese, Cristina Visintin, Anthony M. Vandersteen, P.‐Z. Zhang
Rok vydání:	2000
Předmět:	chemistry.chemical_compound Aglycone Chemistry Aryl Oligoribonucleotides Organic chemistry Protecting group Ribonucleoside Chemical synthesis
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :165-176
ISSN:	1364-5463 1470-4358
Popis:	The comparative rates of acid-catalysed removal of ten 1-aryl-4-methoxypiperidin-4-yl 8 (R = Me) [including the previously reported Ctmp 5 and Fpmp 6] protecting groups for the 2′-hydroxy functions in oligoribonucleotide synthesis are discussed. These studies have led to the development of the 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) protecting group 8 (R = Et, R1 = R2 = H, R3 = Cl) which is both more stable than the Ctmp and Fpmp groups at pH 0.5 and more labile at pH 3.75. The influence of the ribonucleoside aglycone on the stability of the 2′-O-Fpmp and 2′-O-Ctmp protecting groups both at low and high pH is examined.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2ab7d327a022c238822e3df77ad8f007 https://doi.org/10.1039/a908149f Zobrazit plný text záznamu