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Synlett 1999; 1999(2): 204-206
DOI: 10.1055/s-1999-3155
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Diastereoselective Synthesis of 1-Deoxytalonojirimycin

María Ruiz* , Vicente Ojea, José María Quintela
  • *Departamento de Química Fundamental e Industrial, Facultade de Ciencias, Universidade da Coruña, Campus A Zapateira S/N, 15071 A Coruña, Spain; Fax 34-9 81-16 70 65; E-mail: ruizpr@udc.es
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Publication History

Publication Date:
31 December 1999 (online)

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1-Deoxy-d-talonojirimycin ((-)-3) has been synthesised in four steps (38% yield), via a syn-aldol reaction between 2,3-O-isopropylidene-d-erythrose (5) and the stannous salt of the Schöllkopf's bislactim ether 6 followed by the chemoselective oxidation and intramolecular reductive amination of 1,4-diol and lactol key intermediates, 8 and 9, respectively.

imino sugar - syn-aldol - γ-lactol - 1,4-diol oxidation - chiral glycine equivalent