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Synthesis 2010(15): 2626-2630  
DOI: 10.1055/s-0029-1218850
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Unambiguous Syntheses of 3-O-Benzyl-1,5-dideoxy-1,5-imino-d-glucitol and -l-iditol

Zsuzsánna Csíki, Péter Fügedi*
Department of Carbohydrate Chemistry, Chemical Research Center, Hungarian Academy of Sciences, Pusztaszeri út 59-67, 1025 Budapest, Hungary
Fax: +36(1)4381145; e-Mail: pfugedi@chemres.hu;
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Publication History

Received 22 February 2010
Publication Date:
29 June 2010 (online)

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Abstract

Short and unambiguous syntheses of 3-O-benzyl-1,5-dideoxy-1,5-imino-d-glucitol and -l-iditol are described. The compound previously reported as 3-O-benzyl-1,5-dideoxy-1,5-imino-d-glucitol (Roy, A.; Achari, B.; Mandal, S. B. Synthesis 2006, 1035) is shown to be actually 3-O-benzyl-1,5-dideoxy-1,5-imino-l-iditol.

Key words

azasugars - glycosidases - inhibitors - deoxynojirimycin - iminohexitols