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1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions : Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose

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1997

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Wong, Chi-Huey

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The Journal of Organic Chemistry. 1997, 62(7), pp. 2144-2147. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/jo9620066

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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 (31)P 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.

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ISO 690WITTMANN, Valentin, Chi-Huey WONG, 1997. 1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions : Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose. In: The Journal of Organic Chemistry. 1997, 62(7), pp. 2144-2147. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/jo9620066
BibTex
@article{Wittmann19971HTet-9975,
  year={1997},
  doi={10.1021/jo9620066},
  title={1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions : Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose},
  number={7},
  volume={62},
  issn={0022-3263},
  journal={The Journal of Organic Chemistry},
  pages={2144--2147},
  author={Wittmann, Valentin and Wong, Chi-Huey}
}
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