A new approach for the synthesis of 3 '-deoxy-3 '-C-formyl-ribonucleosidesand the synthesis of alternating methylene(methylimino) linked phosphodiester backbone oligonucleotides with 2 '-OH and 2 '-OMe groups

Authors
Prhavc, M Just, G Bhat, B Cook, PD Manoharan, M
Citation
M. Prhavc et al., A new approach for the synthesis of 3 '-deoxy-3 '-C-formyl-ribonucleosidesand the synthesis of alternating methylene(methylimino) linked phosphodiester backbone oligonucleotides with 2 '-OH and 2 '-OMe groups, TETRAHEDR L, 41(51), 2000, pp. 9967-9971
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
51
Year of publication
2000
Pages
9967 - 9971
Database
ISI
SICI code
0040-4039(200012)41:51<9967:ANAFTS>2.0.ZU;2-O
Abstract
A stereoselective synthesis of 3'-deoxy-3'-C-formyl-5-methyluridine 2 is de scribed via the dithiane 4 as the key intermediate. Compound 2 was coupled with 3 into a novel ribo-MMI dimer 1. The dimer was then incorporated into antisense oligonucleotides which were found to have high binding affinity t o the target RNA. (C) 2000 Elsevier Science Ltd. All rights reserved.