Abstract
A protocol for chemoselective deprotection of N,O-acylated ribonucleosides has been developed. Peracylated pyrimidine ribonucleosides subjected to guanidinium nitrate and NaOMe in MeOH/CH2Cl2 at 0 °C undergo high yielding O-deacylation, while even more pronounced chemoselectivity is observed with peracylated purine ribonucleosides as O5′-acyl groups are preserved. Nucleobase-protecting groups (ABz, CBz, GiBu, and UBz) are stable to these conditions, rendering this reagent mixture as a valuable addition to the collection of protecting group protocols in nucleoside chemistry.
Author supplied keywords
Cite
CITATION STYLE
Rigoli, J. W., Østergaard, M. E., Canady, K. M., Guenther, D. C., & Hrdlicka, P. J. (2009). Selective deacylation of peracylated ribonucleosides. Tetrahedron Letters, 50(15), 1751–1753. https://doi.org/10.1016/j.tetlet.2009.01.147
Register to see more suggestions
Mendeley helps you to discover research relevant for your work.
