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An Expeditious Total Synthesis of 5′-Deoxy-toyocamycin and 5′-Deoxysangivamycin
Molecules ( IF 4.2 ) Pub Date : 2019-02-19 , DOI: 10.3390/molecules24040737
Xiangyou Dong , Jie Tang , Chen Hu , Jiang Bai , Haixin Ding , Qiang Xiao

In present paper, an expeditious total synthesis of naturally occurring 5′-deoxytoyocamycin and 5′-deoxysangivamycin was accomplished. Because of the introduction of a benzoyl group at N-6 of 4-amino-5-cyano-6-bromo-pyrrolo[2,3-d]pyrimidine, a Vorbrüggen glycosylation with 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose afforded a completely regioselective N-9 glycosylation product, which is unambiguously confirmed by X-ray diffraction analysis. All of the involved intermediates were well characterized by various spectra.

中文翻译:

5'-脱氧-丰福霉素和5'-脱氧桑吉霉素的快速全合成

在本文中,完成了天然存在的 5'-脱氧丰霉素和 5'-脱氧桑吉霉素的快速全合成。由于在 4-amino-5-cyano-6-bromo-pyrrolo[2,3-d]pyrimidine 的 N-6 处引入了苯甲酰基,因此与 1,2,3-tri-O-乙酰基的 Vorbrüggen 糖基化-5-脱氧-β-D-呋喃核糖提供了完全区域选择性的 N-9 糖基化产物,X 射线衍射分析明确证实了这一点。所有涉及的中间体都通过各种光谱进行了很好的表征。
更新日期:2019-02-19
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