Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides.
Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides.
复制标题
3-羟基氨基-和3-甲氧基氨基-2,3-二脱氧核苷的立体选择性合成。
DOI：
10.1021/acs.orglett.9b03474
复制
发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Bose S
中科院分区：
文献类型：
--
作者：
Bose S
氨基糖苷在医药和生物缀合物化学中被用作关键基序;然而，现有的3′-超亲核胺系统策略并不容易递送脱氧核糖构型的产物。本文报道了从3′-亚胺中间体非对映选择性合成脱氧核糖和脱氧木糖构型的3′-羟基氨基和3′-甲氧基氨基核苷。5′-羟基保护的存在或不存在决定了通过分子间或分子内从BH 3（硼烷）传递氢化物的表面选择性。保护基筛选提供了一个以前未知的3′-甲氧基氨基-脱氧鸟苷衍生物。
Aminonucleosides are used as key motifs in medicinal and bioconjugate chemistry; however, existing strategies toward 3′-hypernucleophilic amine systems do not readily deliverdeoxyribo-configured products. We report diastereoselective syntheses ofdeoxyribo- anddeoxyxylo-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.