Improvement on the Synthesis of Primary Amino Sugar Derivatives via N-Benzyl Intermediates


Primary tosylates 1a-d were converted to the corresponding amino species 3a-d. Benzylamine was proved effective for the substitution of tosylates, using acetonitrile (MeCN) as the solvent of choice and citric acid to remove excess of the reagent from crude products 2a-d. Debenzylation was carried out at circa (ca.) atmospheric pressure of hydrogen gas in the presence of acetic acid (AcOH). The method was also demonstrated in a demo batch experiment for the synthesis of compound 3a on a 50 g scale of 1a.

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M. Corsi, M. Bonanni, G. Catelani, F. D’Andrea, T. Gragnani and R. Bianchini, "Improvement on the Synthesis of Primary Amino Sugar Derivatives via N-Benzyl Intermediates," International Journal of Organic Chemistry, Vol. 3 No. 3A, 2013, pp. 41-48. doi: 10.4236/ijoc.2013.33A005.

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The authors declare no conflicts of interest.


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