4.7 Article

First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside

期刊

MARINE DRUGS
卷 10, 期 4, 页码 881-889

出版社

MDPI
DOI: 10.3390/md10040881

关键词

Vorbruggen glycosylation; total synthesis; pyrrolo[2,3-d]pyrimidine; marine nucleoside

资金

  1. NSFC [20962009, 21062006]
  2. NCET [11-1000]
  3. Education Department of Jiangxi Province [GJJ 11223]
  4. Bureau of Science & Technology of Nanchang City

向作者/读者索取更多资源

4-Amino-7-(5'-deoxy-beta-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 Vorbruggen 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.

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