Synthesis of (S)-2-fluoro-L-daunosamine and (S)-2-fluoro-D-ristosamine |
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| Authors: | H H Baer A Jaworska-Sobiesiak |
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| Affiliation: | 1. Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, 8140, New Zealand;2. Biomolecular Interaction Centre, University of Canterbury, Private Bag 4800, Christchurch, 8140, New Zealand;1. Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;2. Academy of Scientific and Innovative Research (AcSIR), CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;1. Department of Natural Products Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, PR China;2. State Key Laboratory of New Drug and Pharmaceutical Process, Center for Pharmacology, Shanghai Institute of Pharmaceutical Industry, Shanghai 201203, PR China;3. Department of Chemistry, University of Pennsylvania, 231 South 34 Street, Philadelphia, PA 19104-6323, USA;1. Department of Chemistry and Biochemistry, University of Montana, 32 Campus Drive, Missoula, MT 59812, United States;2. Center for Translational Medicine, University of Montana, 32 Campus Drive, Missoula, MT 59812, United States;3. Division of Biological Sciences, University of Montana, 32 Campus Drive, Missoula, MT 59812, United States;1. School of Chemical Engineering, Northwest University/Shaanxi Key Laboratory of Physico-Inorganic Chemistry, Xi''an, Shaanxi 710069, People''s Republic of China;2. Ministry of Science and Technology, The Palace Museum, Beijing 100009, People''s Republic of China;3. College of Life Science, North West Agriculture and Forestry University, Yangling, Shaanxi 712100, People''s Republic of China |
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| Abstract: | Derivatives of (S)-2-fluoro-L-daunosamine and (S)-2-fluoro-D-ristosamine were synthesized, starting ultimately from 2-amino-2-deoxy-D-glucose which was converted, according to the literature, into methyl 2-benzamido-4, 6-O-benzylidene-2-deoxy-3-O-(methylsulfonyl)-alpha-D-glucopyranoside (2). Treatment of 2 with tetrabutylammonium fluoride gave a 63% yield of (known) methyl 3-benzamido-4,6-O-benzylidene-2,3-dideoxy-2-fluoro-alpha-D-altropyran oside (4), together with a 6% yield of its 2-benzamido-2,3-dideoxy-3-fluoro-alpha-D-gluco isomer. From 4, the corresponding 6-bromo-2,3,6-trideoxyglycoside 4-benzoate (6) was obtained by Hanessian-Hullar reaction. Dehydrobromination of 6, followed by catalytic hydrogenation of the resulting 5-enoside, and subsequent debenzoylation and N-trifluoroacetylation, afforded the fluorodaunosaminide, methyl 2,3,6-trideoxy-2-fluoro-3-trifluoroacetamido-beta-L-galactopyranos ide. Reductive debromination of 6, followed by debenzoylation and N-trifluoroacetylation, gave the fluororistosaminide, methyl 2,3,6-trideoxy-2-fluoro-3-trifluoroacetamido-alpha-D-altropyran oside. The 1H-n.m.r. spectra of the new aminofluoro sugars are discussed with respect to the effects of neighboring amino and acylamido substituents on geminal and vicinal 1H-19F coupling constants, in comparison with the reported effects of oxygen substituents. |
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