Synthesis of the antibiotic 1,5-dideoxy-1,5-imino-D-glucitol; concomitant formation of the D-mannitol analogue
β Scribed by H. J. G. Broxterman; G. A. van der Marel; J. H. van Boom; J. J. Neefjes; H. L. Ploegh
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 691 KB
- Volume
- 106
- Category
- Article
- ISSN
- 0165-0513
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π SIMILAR VOLUMES
The utility of bis(tributyltin)oxide-bromine for the selective oxidation of secondary hydroxyl groups in the presence of primary hydroxyl groups has been further demonstrated by the efficient conversions of D-mannitol into r+fructose and 1,5-dideoxy-1,5-imino-D-mannitol Cl-deoxymannojirimycin).
By an Amadori rearrangement of easily available 5-azido-5-deoxy-D-glucofuranose with dibenzylamine and subsequent catalytic hydrogenation of the resulting 5-azido-l-dibenzylamino-l,5dideoxy-D-fructopyranose, the new l-amino-l,2,5-trideoxy-2,5-ilnino-D-mannitol was obtained in only two steps and exce