Synthesis of Sugar Nucleotides by Application of Phosphoramidites

A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate−phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this o...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-12, Vol.73 (23), p.9458-9460
Main Authors: Gold, Henrik, van Delft, Pieter, Meeuwenoord, Nico, Codée, Jeroen D. C, Filippov, Dmitri V, Eggink, Gerrit, Overkleeft, Herman S, van der Marel, Gijs A
Format: Article
Language:English
Subjects:
Acetylglucosamine - chemistry
biosynthesis
Carbohydrates - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
chemical-synthesis
Chemistry
Chemistry, Organic - methods
derivatives
efficient synthesis
Exact sciences and technology
galactose
gdp-fucose
glycosyltransferases
Magnetic Resonance Spectroscopy - methods
Models, Chemical
nucleoside polyphosphates
Nucleosides - chemistry
Nucleosides, nucleotides and oligonucleotides
Nucleotides - chemistry
Organic chemistry
Organophosphorus Compounds - chemistry
Phosphates - chemistry
Phosphites - chemistry
potential chain-terminators
Preparations and properties
udp-glcnac analogs
Uridine Diphosphate - chemistry
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Summary:A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate−phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802021t