Total synthesis of pseudouridine: Via Heck-type C-glycosylation

Cheng Ping Yu; Hsin Yun Chang; Tun Cheng Chien

doi:10.1039/c9nj01012b

Total synthesis of pseudouridine: Via Heck-type C-glycosylation

Cheng Ping Yu, Hsin Yun Chang, Tun Cheng Chien^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

9 引文斯高帕斯（Scopus）

摘要

The reaction of 2,4-dimethoxy-5-iodopyrimidine (8) and 3,5-di-O-tert-butyldimethylsilyl protected ribofuranoid glycal 4 was carried out with Pd(OAc)₂ as the catalyst, PPh₃ as the ligand and Et₃N as the base in DMF at 70 °C followed by desilylation to afford exclusively the β-anomer of 5-(2,3-dideoxy-3-oxoribofuranosyl)-2,4-dimethoxypyrimidine (11) in a very good yield. The subsequent protecting group and functional group interconversions furnished pseudouridine (Ψ, 1).

原文	英語
頁（從 - 到）	8796-8803
頁數	8
期刊	New Journal of Chemistry
卷	43
發行號	22
DOIs	https://doi.org/10.1039/c9nj01012b
出版狀態	已發佈 - 2019

ASJC Scopus subject areas

催化
一般化學
材料化學

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10.1039/c9nj01012b

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title = "Total synthesis of pseudouridine: Via Heck-type C-glycosylation",

abstract = "The reaction of 2,4-dimethoxy-5-iodopyrimidine (8) and 3,5-di-O-tert-butyldimethylsilyl protected ribofuranoid glycal 4 was carried out with Pd(OAc)2 as the catalyst, PPh3 as the ligand and Et3N as the base in DMF at 70 °C followed by desilylation to afford exclusively the β-anomer of 5-(2,3-dideoxy-3-oxoribofuranosyl)-2,4-dimethoxypyrimidine (11) in a very good yield. The subsequent protecting group and functional group interconversions furnished pseudouridine (Ψ, 1).",

author = "Yu, {Cheng Ping} and Chang, {Hsin Yun} and Chien, {Tun Cheng}",

note = "Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.",

year = "2019",

doi = "10.1039/c9nj01012b",

language = "English",

volume = "43",

pages = "8796--8803",

journal = "New Journal of Chemistry",

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publisher = "Royal Society of Chemistry",

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T1 - Total synthesis of pseudouridine

T2 - Via Heck-type C-glycosylation

AU - Yu, Cheng Ping

AU - Chang, Hsin Yun

AU - Chien, Tun Cheng

PY - 2019

Y1 - 2019

N2 - The reaction of 2,4-dimethoxy-5-iodopyrimidine (8) and 3,5-di-O-tert-butyldimethylsilyl protected ribofuranoid glycal 4 was carried out with Pd(OAc)2 as the catalyst, PPh3 as the ligand and Et3N as the base in DMF at 70 °C followed by desilylation to afford exclusively the β-anomer of 5-(2,3-dideoxy-3-oxoribofuranosyl)-2,4-dimethoxypyrimidine (11) in a very good yield. The subsequent protecting group and functional group interconversions furnished pseudouridine (Ψ, 1).

AB - The reaction of 2,4-dimethoxy-5-iodopyrimidine (8) and 3,5-di-O-tert-butyldimethylsilyl protected ribofuranoid glycal 4 was carried out with Pd(OAc)2 as the catalyst, PPh3 as the ligand and Et3N as the base in DMF at 70 °C followed by desilylation to afford exclusively the β-anomer of 5-(2,3-dideoxy-3-oxoribofuranosyl)-2,4-dimethoxypyrimidine (11) in a very good yield. The subsequent protecting group and functional group interconversions furnished pseudouridine (Ψ, 1).

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DO - 10.1039/c9nj01012b

M3 - Article

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VL - 43

SP - 8796

EP - 8803

JO - New Journal of Chemistry

JF - New Journal of Chemistry

IS - 22

ER -

Total synthesis of pseudouridine: Via Heck-type C-glycosylation

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