Stereoselective Syntheses of 3’-Hydroxyamino- and 3’-Methoxyamino-2’,3’-Dideoxynucleosides

Bose, Sritama; Hodgson, David R.W.

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.

Citation

Bose, S., & Hodgson, D. R. (2019). Stereoselective Syntheses of 3’-Hydroxyamino- and 3’-Methoxyamino-2’,3’-Dideoxynucleosides. Organic Letters, 21(22), 9084-9088. https://doi.org/10.1021/acs.orglett.9b03474

• Journal Article Type: Article
• Acceptance Date: Oct 29, 2019
• Online Publication Date: Oct 31, 2019
• Publication Date: Nov 15, 2019
• Deposit Date: Oct 29, 2019
• Publicly Available Date: Nov 1, 2019
• Journal: Organic Letters
• Print ISSN: 1523-7060
• Electronic ISSN: 1523-7052
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 21
• Issue: 22
• Pages: 9084-9088
• DOI: https://doi.org/10.1021/acs.orglett.9b03474
• Public URL: https://durham-repository.worktribe.com/output/1286617