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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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).

Original language	English
Pages (from-to)	8796-8803
Number of pages	8
Journal	New Journal of Chemistry
Volume	43
Issue number	22
DOIs	https://doi.org/10.1039/c9nj01012b
Publication status	Published - 2019

ASJC Scopus subject areas

Catalysis
General Chemistry
Materials Chemistry

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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",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

number = "22",

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TY - JOUR

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).

UR - https://www.scopus.com/pages/publications/85066948617

UR - https://www.scopus.com/pages/publications/85066948617#tab=citedBy

U2 - 10.1039/c9nj01012b

DO - 10.1039/c9nj01012b

M3 - Article

AN - SCOPUS:85066948617

SN - 1144-0546

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

Abstract

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