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Durham University

Department of Chemistry

Publication details for Dr David R.W. Hodgson

Bose, Sritama & Hodgson, David R. W. (2019). Stereoselective Syntheses of 3’-Hydroxyamino- and 3’-Methoxyamino-2’,3’-Dideoxynucleosides. Organic Letters 21(22): 9084-9088.

Author(s) from Durham

Abstract

Aminonucleosides are used as key motifs in medicinal and bioconjugate chemistry; however, existing strategies toward 3′-hypernucleophilic amine systems do not readily deliver deoxyribo-configured products. We report diastereoselective syntheses of deoxyribo- and deoxyxylo-configured 3′-hydroxyamino- and 3′-methoxyamino-nucelosides from 3′-imine intermediates. The presence or absence of the 5′-hydroxyl-group protection dictates facial selectivity via inter- or intramolecular delivery of hydride from BH3 (borane). Protecting group screening gave one access to previously unknown 3′-methoxyamino-deoxyguanosine derivatives.