Methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mamnofuranoside as a divergent intermediate for the synthesis of polyhydroxylated piperidines and pyrrolidines: synthesis of 2,5-dideoxy-2,5-imino-D-mannitol [2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine]

作者： George W.J. Fleet , Paul W. Smith

关键词: Glycoside 、 Nuclear magnetic resonance spectroscopy 、 D-mannitol 、 Chemistry 、 Stereochemistry

摘要: Abstract The synthesis of methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside (1) from D-glucose is reported; the conversions into derivatives 3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside (as precursors for polyhydroxylated piperidines) and hydroxylated pyrrrolidine, 2,5-dideoxy-2,5-imino-D-mannitol [2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine] are described.

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参考文章(7)

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Methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mamnofuranoside as a divergent intermediate for the synthesis of polyhydroxylated piperidines and pyrrolidines: synthesis of 2,5-dideoxy-2,5-imino-D-mannitol [2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine]

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Methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mamnofuranoside as a divergent intermediate for the synthesis of polyhydroxylated piperidines and pyrrolidines: synthesis of 2,5-dideoxy-2,5-imino-D-mannitol [2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine]

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