Chemical transformation of a 1-deoxynojirimycin derivative into 1-deoxymannojirimycin and 1-deoxygalactostatin

Article abstract of DOI:10.1080/07328309808005772

Treatment of 2,3-di-O-benzyl-N-benzyloxycarbonyl-6-O-t-butyldiphenylsilyl-1,5-dideoxy-1,5- imino-D-glucitol (4) with sodium hydride resulted in an intramolecular cyclization concomitant with silyl migration, giving the carbamate derivative 5 in good yield. This was efficiently converted into 1-deoxymannojirimycin (2) via regioselective p-toluenesulfonylation followed by an inversion reaction at the C-2 position. On the other hand, the monochloromethylsulfonate 10 obtained from 4 underwent configurational change at the C-4 position by the action of sodium benzoate. The resulting benzoate 11 was deprotected to afford 1-deoxygalactostatin (3).

Full text of DOI:10.1080/07328309808005772

Journal of Carbohydrate Chemistry
ISSN: 0732-8303 (Print) 1532-2327 (Online) Journal homepage: http://www.tandfonline.com/loi/lcar20
Chemical Transformation of a 1-Deoxynojirimycin
Derivative into 1-Deoxymannojirimycin and 1-
Deoxygalactostatin
Shunya Takahashi & Hiroyoshi Kuzuhara
To cite this article: Shunya Takahashi & Hiroyoshi Kuzuhara (1998) Chemical Transformation of
a 1-Deoxynojirimycin Derivative into 1-Deoxymannojirimycin and 1-Deoxygalactostatin, Journal
of Carbohydrate Chemistry, 17:1, 117-128, DOI: 10.1080/07328309808005772
To link to this article: http://dx.doi.org/10.1080/07328309808005772
Published online: 16 Aug 2006.
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Date: 25 January 2016, At: 01:40