Tetrahedron

… -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 …

GWJ Fleet, PW Smith

文献索引：Fleet, George W. J.; Smith, Paul W. Tetrahedron, 1987 , vol. 43, # 5 p. 971 - 978

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被引用次数: 50

摘要

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