TITLE:
Improvement on the Synthesis of Primary Amino Sugar Derivatives via N-Benzyl Intermediates
AUTHORS:
Massimo Corsi, Marco Bonanni, Giorgio Catelani, Felicia D’Andrea, Tiziana Gragnani, Roberto Bianchini
KEYWORDS:
Amino Sugars; Nucleophilic Substitution; Benzylamine; Primary Tosylates
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.3 No.3A,
November
6,
2013
ABSTRACT: 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.