Suzuki-Miyaura Coupling, Heck Alkenylation, and Amidation of DMTr-Protected 5-Iodo-2'-Deoxyuridine via Palladium-catalyzed Reactions.
DMTr-protected nucleoside
Heck alkenylation
Ruth linker
Suzuki-Miyaura
carboamidation
Journal
Current protocols
ISSN: 2691-1299
Titre abrégé: Curr Protoc
Pays: United States
ID NLM: 101773894
Informations de publication
Date de publication:
Jul 2022
Jul 2022
Historique:
entrez:
27
7
2022
pubmed:
28
7
2022
medline:
30
7
2022
Statut:
ppublish
Résumé
Modification of nucleosides via cross-coupling processes has been carried out extensively on unprotected halonucleosides to produce functionalized nucleosides that are often developed for incorporation into oligonucleotides or used as fluorescent probes. This approach requires protection of the 5'-OH with the 4,4'-dimethoxytrityl (DMTr) group, which is complicated and a common cause of reaction failure. Here we report a method for direct functionalization of 5'-O-DMTr-5-iodo-2'-deoxyuridine via Suzuki-Miyaura cross-coupling, Heck alkenylation, and carboamidation. This approach facilitates rapid synthesis of a variety of C5-substituted 5'-O-DMTr-2'-deoxyuridine derivatives. © 2022 Wiley Periodicals LLC. Basic Protocol 1: Synthesis of the SerrKap palladacycle complex Basic Protocol 2: Suzuki-Miyaura coupling of 5'-O-DMTr-5-iodo-2'-deoxyuridine using SerrKap palladacycle Basic Protocol 3: Heck coupling of 5'-O-DMTr-5-iodo-2'-deoxyuridine using SerrKap palladacycle Basic Protocol 4: Heck coupling of 5'-O-DMTr-5-iodo-2'-deoxyuridine with Ruth linker using Pd(OAc)
Substances chimiques
Nucleosides
0
Oligonucleotides
0
Palladium
5TWQ1V240M
Idoxuridine
LGP81V5245
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e502Subventions
Organisme : Spain Ministry of Science, Innovation, and Universities
ID : RTI2018-098233-B-C21
Organisme : the Fundación SENECA CARM
ID : 20790/PI/18
Informations de copyright
© 2022 Wiley Periodicals LLC.
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