(2S,3S,4S)-4-Amino-2,3,5-trihydroxy-pentanal | 115889-54-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S)-4-Amino-2,3,5-trihydroxy-pentanal
• 英文别名: (2S,3S,4S)-4-amino-2,3,5-trihydroxypentanal
• CAS: 115889-54-8
• 化学式: C₅H₁₁NO₄
• 分子量: 149.147
• InChiKey: YECZZWUIAXEARY-LMVFSUKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-4-Amino-2,3,5-trihydroxy-pentanal 在 钯 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (2S,3S,4R)-2-羟甲基四氢吡咯-3,4-二醇
  参考文献：
  名称：

  Indium-mediated coupling of 3-bromopropenyl acetate with (S)-Garner aldehyde: a route to 1,4-dideoxy-1,4-l-iminoribitol

  摘要：

  The indium organometallic complex generated by metallic indium and 3-bromopropenyl acetate in THF adds to the Garner aldehyde in excellent yield and with high diastereoselectivity; the usefulness of the corresponding anti anti adduct was demonstrated by developing a short synthesis of the title compound, an azasugar known as a glycosidase inhibitor. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.050
• 作为产物：
  描述：

  (4S)-[(1S,2R)-dihydroxybut-3-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 在 Amberlyst(R) 15H 、 臭氧 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 (2S,3S,4S)-4-Amino-2,3,5-trihydroxy-pentanal
  参考文献：
  名称：

  Indium-mediated coupling of 3-bromopropenyl acetate with (S)-Garner aldehyde: a route to 1,4-dideoxy-1,4-l-iminoribitol

  摘要：

  The indium organometallic complex generated by metallic indium and 3-bromopropenyl acetate in THF adds to the Garner aldehyde in excellent yield and with high diastereoselectivity; the usefulness of the corresponding anti anti adduct was demonstrated by developing a short synthesis of the title compound, an azasugar known as a glycosidase inhibitor. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.050