1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions: Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose
Open Access
- 1 April 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (7) , 2144-2147
- https://doi.org/10.1021/jo9620066
Abstract
An improved procedure is described for the efficient and high-yield (76−91%) synthesis of nucleoside diphosphate sugars from the readily available nucleoside 5‘-monophosphomorpholidate and sugar 1-phosphate in the presence of 1H-tetrazole. Comparative kinetic investigations by means of 31P NMR spectroscopy with different additives (1,2,4-triazole, acetic acid, N-hydroxysuccinimide, 4-(dimethylamino)pyridine hydrochloride, perchloric acid) and mass spectrometric analysis suggest that tetrazole acts as an acid and as a nucleophilic catalyst in the pyrophosphate bond formation.Keywords
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