Unusual ring contraction by substitution of 4-O-activated-pentono-1,5-lactams with cyanide. Stereospecific synthesis of 6-amino-1,4,5,6-tetradeoxy-1,4-imino-hexitols |
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| Institution: | 1. Institute of Electro-optical and Materials Science, National Formosa University, Yunlin 63201, Taiwan, ROC;2. Department of Solid State Lighting Technology, Mechanical and Systems Research Laboratories, Industrial Technology Research Institute, Hsinchu 31040, Taiwan, ROC |
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| Abstract: | Reaction of 4-O-sulfonylated 2,3-O-isopropylidene-d-ribo- or -d-lyxo-1,5-lactams with tetrabutylammonium cyanide gave 4-amino-5-C-cyano-4,5-dideoxy-2,3-O-isopropylidene-l-lyxo-5 or -l-ribo-15-1,4-lactams, respectively. A stereospecific ring contraction with inversion at C-4 had taken place in each case. Reduction of the cyano-lactams with LiAlH4 gave 6-amino-1,4,5,6-tetradeoxy-1,4-imino-l-lyxo-6 or -l-ribo-16-hexitol, respectively. The 6-amino-1,4,5,6-tetradeoxy-1,4-imino-l-ribo-hexitol 16 was found to be a moderate inhibitor of α-l-fucosidase with a Ki of 110 μM. |
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