Synthetic Methodologies for C-Nucleosides

Abstract

The study and synthesis of C-nucleosides has been extensive owing to their biological activity and potential as drug candidates for antiviral and anticancer therapy. Numerous synthetic strategies have also been investigated in order to optimize yields and stereoselectivity in the glycosylation reaction. Here we review one class of synthetic methods, direct condensation of a pre-formed aglycon unit with an appropriate sugar component.

Effect of conformational rigidity on the stereoselectivity of nucleophilic additions to five-membered ring bicyclic oxocarbenium ion intermediates

“…These reactions are useful in natural product synthesis 1,2 and can be used to control stereochemistry at tetrasubstituted carbon stereocenters 3-6 . These reactions, many of which proceed through oxocarbenium ion intermediates, are also important in carbohydrate 7 and nucleoside chemistry, 8,9 including the synthesis of non-natural nucleosides 10 .…”

The “Corey's Reagent,” 3,5-di-tert-butyl-1,2-Benzoquinone, as a Modifying Agent in the Synthesis of Fluorescent and Double-Headed Nucleosides

“…[14][15][16] Nucleosides with such substituents as CI, OAc, OAlk, NH 2 , and N 3 groups at 4 -position were synthesized, but the synthesis of nucleosides with two nucleobases failed. [16] We believe this method will prove successful for the synthesis of C-1 nucleoside analogs [17,18] and adenosine receptor agonists [19] and warrants further attention.…”

Synthesis of Differently Protected 1‐C‐Methyl‐Ribofuranoses Intermediates for the Preparation of Biologically Active 1′‐C‐Methyl‐Ribonucleosides

“…[21] It has been reported that ribonolactone 5 reacts with methyllithium at low temperature to Scheme 1: Synthesis of protected D-ribonolactones 5, 6, and 7.…”