2,4-Dinitrophenol: a novel activating reagent in nucleotide synthesis via the phosphoramidite route. Design of new effective phosphitylating reagents

Citation
W. Dabkowski et al., 2,4-Dinitrophenol: a novel activating reagent in nucleotide synthesis via the phosphoramidite route. Design of new effective phosphitylating reagents, TETRAHEDR L, 41(39), 2000, pp. 7535-7539
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
39
Year of publication
2000
Pages
7535 - 7539
Database
ISI
SICI code
0040-4039(20000923)41:39<7535:2ANARI>2.0.ZU;2-#
Abstract
2,4-Dinitrophenol (DNP) is a remarkably efficient activator in the reaction of P(III) amides with nucleosides to give P(III) esters in excellent yield . Typical examples of this novel procedure are presented heroin. Mechanisti c features of the activation were elucidated by model studies of the reacti on of bis(2-cyanoethyl)diisopropylphosphoroamidite with benzyl alcohol. The importance of the initial protonation stage and formation of an intermedia te P(III)-2,4-dinitrophenyl ester were clearly demonstrated by P-31 NMR spe ctroscopy and independent synthesis. New phosphitylating reagents containin g the 2,4-dinitrophenoxy group do not require any activation. (C) 2000 Else vier Science Ltd. All rights reserved.