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About:
Improvement of the C-glycosylation Step for the Synthesis of Remdesivir
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An Entity of Type :
schema:ScholarlyArticle
, within Data Space :
wasabi.inria.fr
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document(s)
Type:
Academic Article
research paper
schema:ScholarlyArticle
New Facet based on Instances of this Class
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type
Academic Article
research paper
schema:ScholarlyArticle
isDefinedBy
Covid-on-the-Web dataset
has title
Improvement of the C-glycosylation Step for the Synthesis of Remdesivir
Creator
Wang, Ke
Zhong, Wu
Xue, Fei
Qin, Yong
Xiang, Ji
Xiao, Dian
Zhou, Xinbo
Gu, Eric
Guo, Xiaowen
Yang, Likai
Zhou, Ruijie
Zhou, Xiaohan
Source
PMC
abstract
[Image: see text] The bulk supply of the antiviral C-nucleoside analogue remdesivir is largely hampered by a low-yielding C-glycosylation step in which the base is coupled to the pentose unit. Here, we disclose a significantly improved methodology for this critical transformation. By utilizing diisopropylamine as a cost-effective additive, the addition reaction furnishes an optimal yield of 75% of the desired ribofuranoside adduct, representing the highest yield obtained thus far for this key step. The method proved suitable for hectogram scale synthesis without column chromatographic operations.
has issue date
2020-08-05
(
xsd:dateTime
)
bibo:doi
10.1021/acs.oprd.0c00310
has license
no-cc
sha1sum (hex)
12f5d1ea103b1a5f1b864eb28e430b1369960001
schema:url
https://doi.org/10.1021/acs.oprd.0c00310
resource representing a document's title
Improvement of the C-glycosylation Step for the Synthesis of Remdesivir
has PubMed Central identifier
PMC7433339
schema:publication
Org Process Res Dev
resource representing a document's body
covid:12f5d1ea103b1a5f1b864eb28e430b1369960001#body_text
is
schema:about
of
named entity 'yield'
named entity 'coupled'
named entity 'adduct'
named entity 'analogue'
named entity 'Improvement'
named entity 'Remdesivir'
named entity 'HIGHEST'
named entity 'PENTOSE'
named entity 'OBTAINED'
named entity 'HECTOGRAM'
named entity 'C-NUCLEOSIDE'
named entity 'SYNTHESIS'
named entity 'FIGURE'
named entity 'KEY'
named entity 'OPTIMAL'
named entity 'EFFECTIVE'
named entity 'TRANSFORMATION'
named entity 'LOW'
named entity 'additive'
named entity 'chromatographic'
named entity 'diisopropylamine'
named entity 'yield'
named entity 'cost-effective'
named entity 'antiviral'
named entity 'remdesivir'
named entity 'glycosylation'
named entity 'Remdesivir'
named entity 'global outbreak'
named entity 'aqueous'
named entity 'flash column chromatography'
named entity 'THF'
named entity 'NMR'
named entity 'remdesivir'
named entity 'diisopropylamine'
named entity 'Vero E6'
named entity 'remdesivir'
named entity 'remdesivir'
named entity 'organic solvents'
named entity 'mol/L'
named entity 'ribose'
named entity 'round-bottom flask'
named entity 'vaccines'
named entity 'diisopropylamine'
named entity 'decagram'
named entity 'n-BuLi'
named entity 'secondary amine'
named entity 'addition reaction'
named entity 'aqueous'
named entity 'remdesivir'
named entity 'remdesivir'
named entity '1.1'
named entity 'lactone'
named entity 'HRMS'
named entity 'mmol'
named entity 'phosphoramidate'
named entity 'remdesivir'
named entity 'lactone'
named entity 'n-hexane'
named entity 'severe acute respiratory syndrome coronavirus 2'
named entity 'mmol'
named entity 'magnesium sulfate'
named entity 'diisopropylamine'
named entity 'clinical trials'
named entity 'SARS-CoV'
named entity 'Emergency Use Authorization'
named entity 'aqueous'
named entity 'quaternary amine'
named entity 'remdesivir'
named entity 'EtOAc'
named entity 'small-molecule drug'
named entity 'lactone'
named entity 'argon'
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