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Synthesis 1995; 1995(7): 787-794
DOI: 10.1055/s-1995-4009
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Deoxyiminoalditols from Aldonolactones; IV: Preparation of 1,5-Dideoxy-1,5-iminoheptitols with L-glycero-D-manno, D-glycero-L-gulo and L-glycero-D-altro Configuration

Inge Lundt* , Robert Madsen
  • *Department of Organic Chemistry, The Technical University of Denmark, Building 201, DK-2800 Lyngby, Denmark, Fax +45(45)933968
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Publication Date:
31 December 2000 (online)

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Three novel 1,5-dideoxy-1,5-iminoheptitols 4, 12 and 20 were prepared by a convenient two-step procedure from 2,7-dibromo-2,7-dideoxyheptono-1,4-lactones 1, 9 and 17, respectively. The dibromolactones were either reacted directly with ammonia to give iminoheptonic acids which were then reduced, or the dibromolactones were first reduced to dibromoheptitols which were then treated with ammonia. The ring closure of the dibromo compounds was shown to proceed via epoxides. In addition, chain elongation of D-mannose and D-galactose with cyanide was carried out and the resulting heptonic acids were used for preparation of four novel bromodeoxyheptonolactones 6, 9, 14 and 17.

bromodeoxyheptonolactones/heptitols - epoxides - 1,5-iminoheptitols - glycosidase inhibitors