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

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

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-p...

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Bibliographic Details
Main Authors: Jianyun Sun, Yanhui Dou, Haixin Ding, Ruchun Yang, Qi Sun, Qiang Xiao
Format: Article
Language:English
Published: MDPI AG 2012-04-01
Series:Marine Drugs
Subjects:
Vorbrüggen glycosylation
total synthesis
pyrrolo[2,3-d]pyrimidine
marine nucleoside
Online Access:http://www.mdpi.com/1660-3397/10/4/881/
Description
Summary: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.
ISSN:1660-3397

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