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Synthesis of Phostone‐Constrained Nucleic Acid (P‐CNA) Dinucleotides Through Intramolecular Arbuzov's Reaction
Author(s) -
Catana DanAndrei,
Maturano Marie,
Payrastre Corinne,
Lavedan Pierre,
Tarrat Nathalie,
Escudier JeanMarc
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.201101061
Subject(s) - chemistry , intramolecular force , phosphonate , sugar phosphates , nucleic acid , bromide , zinc bromide , stereochemistry , wittig reaction , lithium (medication) , combinatorial chemistry , phosphate , organic chemistry , catalysis , biochemistry , endocrinology , medicine
P‐CNAs are dinucleotide building blocks in which the torsional angles α and β of the sugar/phosphate backbone are constrained to non‐canonical values within a cyclic phosphonate structure (phostone) synthesised by diastereoselective intramolecular Arbuzov reaction. The reaction has been improved through the use of microwave activation and addition of lithium bromide.