Synthesis of 2-C-Substituted 5-Deoxyglucals from D-Ribose: Access to 2-C-Substituted 5-Deoxyglycosides and -Nucleosides

The synthesis of 2-C-substituted 5-deoxyglucals from D-ribose, by using a nickel-catalyzed cross-coupling reaction of 2-iodo-5-deoxyglucals with Grignard reagents, is reported. The obtained 2-C-substituted 5-deoxyglucals were then transformed into 2-C-substituted 5-deoxyglycosides and 2-C-substituted 5-deoxynucleosides. During this work, structures published in the literature were reassigned.

Automated summary

This study reports the synthesis of 2-C-substituted 5-deoxyglucals from D-ribose using a nickel-catalyzed cross-coupling reaction. The obtained compounds were further transformed into 2-C-substituted 5-deoxyglycosides and 2-C-substituted 5-deoxynucleosides. The work also involves the reassignment of previously published structures.