Organocatalytic Direct α-Selective N-Glycosylation of Amide with Glycosyl Trichloroacetimidate.

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Abstrakt

Tytuł:: Organocatalytic Direct α-Selective N-Glycosylation of Amide with Glycosyl Trichloroacetimidate.
Autorzy:: Li S; Graduate School of Advanced Integrated Studies in Human Survivability, Kyoto University.
Kobayashi Y; Graduate School of Pharmaceutical Sciences, Kyoto University.
Takemoto Y; Graduate School of Advanced Integrated Studies in Human Survivability, Kyoto University.; Graduate School of Pharmaceutical Sciences, Kyoto University.
Źródło:: Chemical & pharmaceutical bulletin [Chem Pharm Bull (Tokyo)] 2018; Vol. 66 (7), pp. 768-770.
Typ publikacji:: Journal Article
Język:: English
Imprint Name(s):: Original Publication: Tokyo, Pharmaceutical Society of Japan.
MeSH Terms:: Acetamides/*chemistry
Amides/*chemistry
Chloroacetates/*chemistry
Glycosides/*chemical synthesis
Thiourea/*chemistry
Catalysis ; Glycosides/chemistry ; Glycosylation ; Molecular Structure
Contributed Indexing:: Keywords: glycosylation; green chemistry; halogen bond; hydrogen bond; organocatalyst
Substance Nomenclature:: 0 (Acetamides)
0 (Amides)
0 (Chloroacetates)
0 (Glycosides)
GYV9AM2QAG (Thiourea)
I8BL3305RO (trichloroacetamide)
Entry Date(s):: Date Created: 20180703 Date Completed: 20180725 Latest Revision: 20180725
Update Code:: 20240105
DOI:: 10.1248/cpb.c18-00255
PMID:: 29962459
: Czasopismo naukowe

Through the synergistic catalytic effect of the halogen bond (XB) donor and thiourea catalyst, a direct α-selective N-glycosylation of the amide residue of asparagine derivative was achieved using readily accessible glycosyl trichloroacetimidate. n-Butyl methyl ether was found to be the most suitable solvent for the α-selectivity.

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