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Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides.

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.

SUBMITTER: Bose S

PROVIDER: S-EPMC7007280 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides.

Bose Sritama S Hodgson David R W DRW

Organic letters 20191031 22

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 ...[more]

PMID: 31668079

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