A simple access to the D-mannosidase inhibitor, 1-deoxymannojirimycin |
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Authors: | Spreitz Josef Stütz Arnold E Wrodnigg Tanja M |
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Institution: | Glycogroup, Institut für Organische Chemie der Technischen Universit?t Graz, Stremayrgasse 16, A-8010 Graz, Austria. |
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Abstract: | Crystalline 1,3,4,5-tetra-O-acetyl-6-bromo-6-deoxy-keto-D-fructose was prepared by reaction of 1,3,4,5-tetra-O-acetyl-D-fructopyranose with triphenylphosphane dibromide in dichloromethane. Subsequent deprotection followed by reaction of the free 6-bromodeoxyfructofuranose with sodium azide in N,N-dimethylformamide furnished the corresponding 6-azidodeoxyketose. Catalytic hydrogenation led to 1-deoxymannojirimycin in 27% overall yield from 1,3,4,5-tetra-O-acetyl-D-fructopyranose. This access is simple, inexpensive, high-yielding and clearly suitable for multigram preparations. |
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Keywords: | 1-Deoxymannojirimycin d-Mannosidase inhibitor" target="_blank">d-Mannosidase inhibitor Open-chain ketose 1 3 4 d-fructose" target="_blank">5-Tetra-O-acetyl-6-bromo-6-deoxy-keto-d-fructose |
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