Polyhydroxylated pyrrolidines from sugar lactomes: Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol from d-galactonolactone and syntheses of 1,4-dideoxy-1,4-imino-d-allitol, 1,4-dideoxy-1,4-imino-d-ribitol,and (2s,3r,4s)-3,4-dihydroxyproline from d-gulonolactone |
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Institution: | 3. From the Department of Medical Biochemistry and Biophysics, Umeå University, SE-901 87 Umeå, Sweden and;4. Institute of Infection, Immunity and Inflammation, College of Medical, Veterinary and Life Sciences, University of Glasgow, Glasgow G12 8TA, Scotland, United Kingdom;1. Chemical Engineering Department, The Pennsylvania State University, University Park, PA 16802, United States;2. Pharmaceutical Sciences, Merck & Co., Inc., West Point, PA, United States;1. Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow 226 031, India;2. Division of Microbiology, CSIR-Central Drug Research Institute, Lucknow, 226 031, India |
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Abstract: | The use of readily available sugar lactones in the synthesis of polyhydroxylated pyrrolidines is illustrated by the preparation of the glucosidase inhibitor 1,4-dideoxy-1, 4-imino-D-glucitol from D-galactonolactone and by the conversion of D-gulonolactone into 1,4-dideoxy-l,4-imino-D-allitol, 1,4-dideoxy-l,4-imino-D-ribitol, and (2S,3R,4S)-3,4-dihydroxyproline. |
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