Stereoselective Synthesis of 4'-Selenonucleosides via the Seleno-Michael Reaction

Pramod K Sahu; Dnyandev B Jarhad; Gyudong Kim; Lak Shin Jeong

doi:10.1002/cpnc.27

Stereoselective Synthesis of 4'-Selenonucleosides via the Seleno-Michael Reaction

Curr Protoc Nucleic Acid Chem. 2017 Jun 19:69:14.13.1-14.13.15. doi: 10.1002/cpnc.27.

Authors

Pramod K Sahu¹, Dnyandev B Jarhad¹, Gyudong Kim¹, Lak Shin Jeong¹

Affiliation

¹ Laboratory of Medicinal Chemistry, College of Pharmacy, Seoul National University, Seoul, South Korea.

PMID: 28628205
DOI: 10.1002/cpnc.27

Abstract

5'-Homo-4'-selenonucleosides, a class of next-generation nucleosides, are synthesized from D-ribose via a 4-selenosugar intermediate. The key step in synthesizing this intermediate is a seleno-Michael reaction. 5'-Homo-4'-selenouridine and -adenosine are prepared using Pummerer-type and Vorbrüggen condensation, respectively. © 2017 by John Wiley & Sons, Inc.

Keywords: 4′-selenonucleoside; Pummerer-type reaction; Vorbrüggen condensation; seleno-Michael.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbon-13 Magnetic Resonance Spectroscopy
Nucleosides / chemical synthesis*
Nucleosides / chemistry
Proton Magnetic Resonance Spectroscopy
Selenium / chemistry*
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism

Substances

Nucleosides
Selenium