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...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2012-04-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/10/4/881/ |
| _version_ | 1828109891284238336 |
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| author | Jianyun Sun Yanhui Dou Haixin Ding Ruchun Yang Qi Sun Qiang Xiao |
| author_facet | Jianyun Sun Yanhui Dou Haixin Ding Ruchun Yang Qi Sun Qiang Xiao |
| author_sort | Jianyun Sun |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-04-11T11:11:21Z |
| format | Article |
| id | doaj.art-fe5dea74ee6244df97e3d2e8a67d1c87 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T11:11:21Z |
| publishDate | 2012-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-fe5dea74ee6244df97e3d2e8a67d1c872022-12-22T04:27:30ZengMDPI AGMarine Drugs1660-33972012-04-0110488188910.3390/md10040881First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine NucleosideJianyun SunYanhui DouHaixin DingRuchun YangQi SunQiang Xiao4-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.http://www.mdpi.com/1660-3397/10/4/881/Vorbrüggen glycosylationtotal synthesispyrrolo[2,3-d]pyrimidinemarine nucleoside |
| spellingShingle | Jianyun Sun Yanhui Dou Haixin Ding Ruchun Yang Qi Sun Qiang Xiao First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside Marine Drugs Vorbrüggen glycosylation total synthesis pyrrolo[2,3-d]pyrimidine 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 | Vorbrüggen glycosylation total synthesis pyrrolo[2,3-d]pyrimidine marine nucleoside |
| url | http://www.mdpi.com/1660-3397/10/4/881/ |
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