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First total synthesis of a naturally occurring iodinated 5'-deoxyxylofuranosyl marine nucleoside.
Marine Drugs ( IF 4.9 ) Pub Date : 2012-04-10 , DOI: 10.3390/md10040881
Jianyun Sun 1 , Yanhui Dou 1 , Haixin Ding 1 , Ruchun Yang 1 , Qi Sun 1 , Qiang Xiao 1
Affiliation  

4-Amino-7-(5'-deoxy-β-D-xylofuranosyl)-5-iodo-pyrrolo[2,3-d]pyrimidine 1, an unusual naturally occurring marine nucleoside isolated from an ascidan, Diplosoma sp., was synthesized from D-xylose in seven steps with 28% overall yield on 10 g scale. The key step was Vorbrüggen glycosylation of 5-iodo-pyrrolo[2,3-d]pyrimidine with 5-deoxy-1,2-O-diacetyl-3-O-benzoyl-D-xylofuranose. Its absolute configuration was confirmed.

中文翻译:

首次全合成天然存在的碘化 5'-脱氧呋喃糖基海洋核苷。

4-Amino-7-(5'-deoxy-β-D-xylofuranosyl)-5-iodo-pyrrolo[2,3-d]pyrimidine 1,一种不寻常的天然存在的海洋核苷,从海鞘 Diplosoma sp. 中分离出来。由 D-木糖分 7 步合成,10 g 规模的总产率为 28%。关键步骤是 5-碘代吡咯并[2,3-d]嘧啶与 5-deoxy-1,2-O-diacetyl-3-O-benzoyl-D-xylofuranose 的 Vorbrüggen 糖基化。其绝对构型得到确认。
更新日期:2019-11-01
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