Maleimide-Dimethylfuran exo Adducts: Effective Maleimide Protection in the Synthesis of Oligonucleotide Conjugates
Organic Letters2011Vol. 13(16), pp. 4364–4367
Citations Over TimeTop 18% of 2011 papers
Abstract
The reaction of maleimide-containing compounds with 2,5-dimethylfuran gives a mixture of exo and endo isomers from which the exo cycloadduct can be easily isolated taking advantage of its stability in concentrated aqueous ammonia. Bifunctional compounds incorporating a dimethylfuran-protected maleimide (exo adduct) have been attached to resin-linked oligonucleotide chains. Removal of protecting groups masking oligonucleotide functionalities followed by retro-Diels-Alder maleimide deprotection affords maleimido-oligonucleotides suitable for conjugation, as assessed by their reaction with different thiols.
Related Papers
- → Study of the Diels–Alder and retro-Diels–Alder reaction between furan derivatives and maleimide for the creation of new materials(2015)213 cited
- → The application of the Diels-Alder reaction to polymer syntheses based on furan/maleimide reversible couplings(2005)36 cited
- → The unexpected product of Diels-Alder reaction between “indanocyclon” and maleimide(2016)7 cited
- → N-(2,3,4,5,6-Pentafluorophenyl)maleimide as a Powerful Dienophile in Dearomatizing Diels-Alder Reactions(2014)4 cited
- → ChemInform Abstract: The Mitsunobu Reaction: A Novel Method for the Synthesis of Bifunctional Maleimide Linkers.(1994)