Regioselective 2,7-dimethyl-9-phenyl xanthen-9-yl protection and deprotection of nucleosides under mild conditions

[Display omitted] A simple and efficient protocol is developed for regioselective protection of primary hydroxyl group of nucleosides using 2,7-dimethylpixyliumtrifluoroacetate, prepared in-situ from 2,7-dimethyl-9-phenylxanthen-9-ol (DMPx-OH) and trifluoroacetic anhydride (TFAA). Furthermore deprot...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 121; pp. 154480 - 154484
Main Authors Samudrala, Rajendra Prasad, Penjarla, Srishylam, Gundla, Rambabu, Purna Chandra Rao, B.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.05.2023
Elsevier
Subjects
Chemistry
Chemistry, Organic
DMPx-group
Nucleosides
Physical Sciences
Protection and Deprotection
Regioselectivity
Science & Technology
Nucleosides
Regioselectivity
Protection and Deprotection
DMPx-group
CHEMICAL-SYNTHESIS
OLIGONUCLEOTIDES
Online AccessGet full text

Cover

More Information
Summary:[Display omitted] A simple and efficient protocol is developed for regioselective protection of primary hydroxyl group of nucleosides using 2,7-dimethylpixyliumtrifluoroacetate, prepared in-situ from 2,7-dimethyl-9-phenylxanthen-9-ol (DMPx-OH) and trifluoroacetic anhydride (TFAA). Furthermore deprotection of DMPx group is accomplished with TFAA in shorter reaction times with excellent yields in DCM:Methanol solvent system. Both procedures are successfully implemented on gram scale for synthesis of natural as well as other modified nucleosides. Various functional groups such as benzoyl, benzyl, tetrahydropyranyl, TBDPS, and formamidine groups are intact during protection with DMPx-group.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2023.154480