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

Bose, Sritama; Hodgson, David R.W.

doi:10.1021/acs.orglett.9b03474

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

Bose, Sritama; Hodgson, David R.W.

Authors

Sritama Bose

Professor David Hodgson d.r.w.hodgson@durham.ac.uk
Professor

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

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