First total synthesis of a naturally occurring iodinated 5'-deoxyxylofuranosyl marine nucleoside
Jianyun Sun1, Yanhui Dou1, Haixin Ding1
1Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China.
Abstract:
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.
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