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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Autores principales: Sun, Jianyun, Dou, Yanhui, Ding, Haixin, Yang, Ruchun, Sun, Qi, Xiao, Qiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3366680/
https://www.ncbi.nlm.nih.gov/pubmed/22690148
http://dx.doi.org/10.3390/md10040881
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author Sun, Jianyun
Dou, Yanhui
Ding, Haixin
Yang, Ruchun
Sun, Qi
Xiao, Qiang
author_facet Sun, Jianyun
Dou, Yanhui
Ding, Haixin
Yang, Ruchun
Sun, Qi
Xiao, Qiang
author_sort Sun, Jianyun
collection PubMed
description 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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spelling pubmed-33666802012-06-11 First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside Sun, Jianyun Dou, Yanhui Ding, Haixin Yang, Ruchun Sun, Qi Xiao, Qiang Mar Drugs Communication 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. MDPI 2012-04-10 /pmc/articles/PMC3366680/ /pubmed/22690148 http://dx.doi.org/10.3390/md10040881 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Communication
Sun, Jianyun
Dou, Yanhui
Ding, Haixin
Yang, Ruchun
Sun, Qi
Xiao, Qiang
First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside
title First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside
title_full First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside
title_fullStr First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside
title_full_unstemmed First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside
title_short First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside
title_sort first total synthesis of a naturally occurring iodinated 5′-deoxyxylofuranosyl marine nucleoside
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3366680/
https://www.ncbi.nlm.nih.gov/pubmed/22690148
http://dx.doi.org/10.3390/md10040881
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