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

Marine Drugs

Jianyun Sun¹  Yanhui Dou¹  Haixin Ding¹  Ruchun Yang¹  Qi Sun¹ 

[1] Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China;

关键词: Vorbrüggen glycosylation;    total synthesis;    pyrrolo[2;    3-d]pyrimidine;    marine nucleoside;   

DOI  :  10.3390/md10040881

来源: mdpi

【 摘 要 】

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.

【 授权许可】

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© 2012 by the authors; licensee MDPI, Basel, Switzerland.