(R/S)-3-[(1R)-1-Acetylamino-2,3:4,5-di-O-isopropyliden-D-arabinitol-1-yl]-4,5-dihydro-isoxazol-5-carbonsaeure-methylester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R/S)-3-[(1R)-1-Acetylamino-2,3:4,5-di-O-isopropyliden-D-arabinitol-1-yl]-4,5-dihydro-isoxazol-5-carbonsaeure-methylester
• 英文别名: methyl 3-[(R)-acetamido-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-4,5-dihydro-1,2-oxazole-5-carboxylate
• 化学式: C₁₈H₂₈N₂O₈
• 分子量: 400.429
• InChiKey: AZGSPBINXXRYPH-XSISWNRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 2-Acetamido-1,2-didesoxy-3,4:5,6-di-O-isopropyliden-1-nitro-D-mannitol 在 异氰酸苯酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以74%的产率得到(R/S)-3-[(1R)-1-Acetylamino-2,3:4,5-di-O-isopropyliden-D-arabinitol-1-yl]-4,5-dihydro-isoxazol-5-carbonsaeure-methylester
  参考文献：
  名称：

  Kettenverlängerung von 1-desoxy-1-nitroalditolen durch nitriloxid-cycloaddition. Synthese von 4-N-substituierten 3,4-didesoxy-2-ulosonsäuren

  摘要：

  Treatment of protected nitroalditols 1a or 2 with silylenolpyruvate (3) or methyl acrylate leads via nitrile oxide cycloadditon to cycle-tautomers of oximes, 5 or 4, respectively 4,5-dihydro-isoxazole 6. N-Acetyl-4-deoxy-4-(E/Z)-hydroxyimino-neuraminic acid (7) is obtained by deprotection of 4. Hydrogenation of 7 yields N-acetyl-4-amino-4-deoxy-neuraminic acid (9) and pentahydroxy-nononic acids 12a,b. The synthesis is useful for the chain extension of protected nitroalditols 13a and 20a, to give the corresponding oximes 15 and 22. This work provides a general method for the extension of sugar chains by three C-atoms and thus a novel synthesis of cr-keto acids containing an oxime and amino function. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00168-9

文献信息

• Kettenverlängerung von 1-desoxy-1-nitroalditolen durch nitriloxid-cycloaddition. Synthese von 4-N-substituierten 3,4-didesoxy-2-ulosonsäuren
  作者：Hans Mack、Reinhard Brossmer

  DOI：10.1016/s0040-4020(98)00168-9

  日期：1998.4

  Treatment of protected nitroalditols 1a or 2 with silylenolpyruvate (3) or methyl acrylate leads via nitrile oxide cycloadditon to cycle-tautomers of oximes, 5 or 4, respectively 4,5-dihydro-isoxazole 6. N-Acetyl-4-deoxy-4-(E/Z)-hydroxyimino-neuraminic acid (7) is obtained by deprotection of 4. Hydrogenation of 7 yields N-acetyl-4-amino-4-deoxy-neuraminic acid (9) and pentahydroxy-nononic acids 12a,b. The synthesis is useful for the chain extension of protected nitroalditols 13a and 20a, to give the corresponding oximes 15 and 22. This work provides a general method for the extension of sugar chains by three C-atoms and thus a novel synthesis of cr-keto acids containing an oxime and amino function. (C) 1998 Elsevier Science Ltd. All rights reserved.