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On the Compatibility of Azides in Phosphoramidite‐Based Couplings: Synthesis of a Novel, Convertible Azido‐Functionalized CyPLOS Analogue
Author(s) -
Coppola Cinzia,
Simeone Luca,
De Napoli Lorenzo,
Montesarchio Daniela
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001057
Subject(s) - phosphoramidite , chemistry , combinatorial chemistry , surface modification , compatibility (geochemistry) , nucleoside , nuclear magnetic resonance spectroscopy , organic chemistry , stereochemistry , oligonucleotide , dna , biochemistry , geochemistry , geology
Abstract With the aim of preparing a library of ion transporters based on a CyPLOS (cyclic phosphate‐linked oligosaccharide) backbone, we describe the synthesis of a novel azido‐derivatized CyPLOS analogue that is tailored for practical post‐synthetic functionalization with a variety of labels. As a prerequisite for the effective preparation of this phosphate‐linked macrocycle, the compatibility of azido alcohols as coupling agents in phosphoramidite synthetic protocols was preliminarily investigated in solution by using 31 P NMR spectroscopy to monitor the standard coupling of a nucleoside 3′‐phosphoramidite with suitable model alcohols and azides.