First Total Synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps">d</span>-Glucopyranosyl Tubercidin
The first total synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps;">d</span>-glucopyranosyl tubercidin was successfully developed. It is a structurally unique disaccharide 7-deazapurine nucleoside exhibiting fungicidal activity, and was isolated from...
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MDPI AG
2020-07-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/8/398 |
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| author | Wenliang Ouyang Haiyang Huang Ruchun Yang Haixin Ding Qiang Xiao |
| author_facet | Wenliang Ouyang Haiyang Huang Ruchun Yang Haixin Ding Qiang Xiao |
| author_sort | Wenliang Ouyang |
| collection | DOAJ |
| description | The first total synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps;">d</span>-glucopyranosyl tubercidin was successfully developed. It is a structurally unique disaccharide 7-deazapurine nucleoside exhibiting fungicidal activity, and was isolated from blue-green algae. The total synthesis was accomplished in eight steps with 27% overall yield from commercially available 1-<i>O</i>-acetyl-2,3,5-tri-<i>O</i>-benzoyl-β-<span style="font-variant: small-caps;">d</span>-ribose. The key step involves stereoselective α-<i>O</i>-glycosylation of the corresponding 7-bromo-6-chloro-2′,3′-<i>O</i>-isopropylidene-β-<span style="font-variant: small-caps;">d</span>-tubercidin with 2,3,4,6-tetra-<i>O</i>-benzyl-glucopyranosyl trichloroacetimidate. All spectra are in accordance with the reported data for natural 5′-<i>O</i>-α-<span style="font-variant: small-caps;">d</span>-glucopyranosyl tubercidin. Meanwhile, 5′-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl tubercidin was also prepared using the same strategy. |
| first_indexed | 2024-03-10T18:08:26Z |
| format | Article |
| id | doaj.art-b3e67be8856d4fef927a20f78eba2042 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T18:08:26Z |
| publishDate | 2020-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-b3e67be8856d4fef927a20f78eba20422023-11-20T08:18:07ZengMDPI AGMarine Drugs1660-33972020-07-0118839810.3390/md18080398First Total Synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps">d</span>-Glucopyranosyl TubercidinWenliang Ouyang0Haiyang Huang1Ruchun Yang2Haixin Ding3Qiang Xiao4Jiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, ChinaJiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, ChinaJiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, ChinaJiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, ChinaJiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, ChinaThe first total synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps;">d</span>-glucopyranosyl tubercidin was successfully developed. It is a structurally unique disaccharide 7-deazapurine nucleoside exhibiting fungicidal activity, and was isolated from blue-green algae. The total synthesis was accomplished in eight steps with 27% overall yield from commercially available 1-<i>O</i>-acetyl-2,3,5-tri-<i>O</i>-benzoyl-β-<span style="font-variant: small-caps;">d</span>-ribose. The key step involves stereoselective α-<i>O</i>-glycosylation of the corresponding 7-bromo-6-chloro-2′,3′-<i>O</i>-isopropylidene-β-<span style="font-variant: small-caps;">d</span>-tubercidin with 2,3,4,6-tetra-<i>O</i>-benzyl-glucopyranosyl trichloroacetimidate. All spectra are in accordance with the reported data for natural 5′-<i>O</i>-α-<span style="font-variant: small-caps;">d</span>-glucopyranosyl tubercidin. Meanwhile, 5′-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl tubercidin was also prepared using the same strategy.https://www.mdpi.com/1660-3397/18/8/398total synthesisnatural product7-deazapurine nucleosidedisaccharide nucleosidetubercidin |
| spellingShingle | Wenliang Ouyang Haiyang Huang Ruchun Yang Haixin Ding Qiang Xiao First Total Synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps">d</span>-Glucopyranosyl Tubercidin Marine Drugs total synthesis natural product 7-deazapurine nucleoside disaccharide nucleoside tubercidin |
| title | First Total Synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps">d</span>-Glucopyranosyl Tubercidin |
| title_full | First Total Synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps">d</span>-Glucopyranosyl Tubercidin |
| title_fullStr | First Total Synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps">d</span>-Glucopyranosyl Tubercidin |
| title_full_unstemmed | First Total Synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps">d</span>-Glucopyranosyl Tubercidin |
| title_short | First Total Synthesis of 5′-<i>O</i>-α-<span style="font-variant: small-caps">d</span>-Glucopyranosyl Tubercidin |
| title_sort | first total synthesis of 5 i o i α span style font variant small caps d span glucopyranosyl tubercidin |
| topic | total synthesis natural product 7-deazapurine nucleoside disaccharide nucleoside tubercidin |
| url | https://www.mdpi.com/1660-3397/18/8/398 |
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