专利号:US-4362720-A 优先权日:1977-04-14 标题:Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals 发明人:LEMIEUX RAYMOND U; RATCLIFFE R MURRAY 权利人:CHEMBIOMED LTD 摘要:O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.
专利号:US-4308376-A 优先权日:1977-04-14 标 题 :Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals 发明人:LEMIEUX RAYMOND U; RATCLIFFE R MURRAY 权利人:CHEMBIOMED LTD 摘要:O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.
专利号:US-4195174-A 优先权日:1977-04-14 标题 :Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
参考文献:10.1016/j.bmc.2009.08.049 摘要:Stokmaier D, Khorev O, Cutting B, Born R, Ricklin D, Ernst TO, Böni F, Schwingruber K, Gentner M, Wittwer M, Spreafico M, Vedani A, Rabbani S, Schwardt O, Ernst B. Design, synthesis and evaluation of monovalent ligands for the asialoglycoprotein receptor (ASGP-R). Bioorg Med Chem. 2009 Oct 15;17(20):7254–64. doi: 10.1016/j.bmc.2009.08.049.