5-amino-5-deoxy-2,3-O-isopropylidene-4-O-methanesulfonyl-D-lyxono-1,5-lactam | 286859-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-amino-5-deoxy-2,3-O-isopropylidene-4-O-methanesulfonyl-D-lyxono-1,5-lactam
• 英文别名: [(3aS,7R,7aR)-2,2-dimethyl-4-oxo-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridin-7-yl] methanesulfonate
• CAS: 286859-25-4
• 化学式: C₉H₁₅NO₆S
• 分子量: 265.287
• InChiKey: GFOBJMRZPMCJMY-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  氰化四丁基铵 、 5-amino-5-deoxy-2,3-O-isopropylidene-4-O-methanesulfonyl-D-lyxono-1,5-lactam 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以62%的产率得到4-amino-5-C-cyano-4,5-dideoxy-2,3-O-isopropylidene-L-ribono-1,4-lactam
  参考文献：
  名称：

  Unusual ring contraction by substitution of 4-O-activated-pentono-1,5-lactams with cyanide. Stereospecific synthesis of 6-amino-1,4,5,6-tetradeoxy-1,4-imino-hexitols

  摘要：

  Reaction of 4-O-sulfonylated 2,3-O-isopropylidene-D-ribo- or -D-lyxo-1,5-lactams with tetrabutylammonium cyanide gave 4-amino-5-C-cyano-4,5-dideoxy-2,3-O-isopropylidene-L-lyxo-5 or -L-ribo-15-1,4-lactams, respectively. A stereospecific ring contraction with inversion at C-4 had taken place in each case. Reduction of the cyanolactams with LiAlH4 gave 6-amino-1,4,5,6-tetradeoxy-1,4-imino-L-lyxo-6 or -L-ribo-16-hexitol, respectively. The 6-amino-1,4,5,6-tetradeoxy-1,4-imino-L-ribo-hexitol 16 was found to be a moderate inhibitor of alpha-L-fucosidase with a K-i of 110 mu M. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00536-4
• 作为产物：
  描述：

  D-Lyxonsaeure-methylester 在 吡啶 、 ammonium hydroxide 、 甲烷磺酸 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 46.83h， 生成 5-amino-5-deoxy-2,3-O-isopropylidene-4-O-methanesulfonyl-D-lyxono-1,5-lactam
  参考文献：
  名称：

  Unusual ring contraction by substitution of 4-O-activated-pentono-1,5-lactams with cyanide. Stereospecific synthesis of 6-amino-1,4,5,6-tetradeoxy-1,4-imino-hexitols

  摘要：

  Reaction of 4-O-sulfonylated 2,3-O-isopropylidene-D-ribo- or -D-lyxo-1,5-lactams with tetrabutylammonium cyanide gave 4-amino-5-C-cyano-4,5-dideoxy-2,3-O-isopropylidene-L-lyxo-5 or -L-ribo-15-1,4-lactams, respectively. A stereospecific ring contraction with inversion at C-4 had taken place in each case. Reduction of the cyanolactams with LiAlH4 gave 6-amino-1,4,5,6-tetradeoxy-1,4-imino-L-lyxo-6 or -L-ribo-16-hexitol, respectively. The 6-amino-1,4,5,6-tetradeoxy-1,4-imino-L-ribo-hexitol 16 was found to be a moderate inhibitor of alpha-L-fucosidase with a K-i of 110 mu M. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00536-4

文献信息

• Unusual ring contraction by substitution of 4-O-activated-pentono-1,5-lactams with cyanide. Stereospecific synthesis of 6-amino-1,4,5,6-tetradeoxy-1,4-imino-hexitols
  作者：Michael Godskesen、Inge Lundt、Inger Søtofte

  DOI：10.1016/s0957-4166(99)00536-4

  日期：2000.2

  Reaction of 4-O-sulfonylated 2,3-O-isopropylidene-D-ribo- or -D-lyxo-1,5-lactams with tetrabutylammonium cyanide gave 4-amino-5-C-cyano-4,5-dideoxy-2,3-O-isopropylidene-L-lyxo-5 or -L-ribo-15-1,4-lactams, respectively. A stereospecific ring contraction with inversion at C-4 had taken place in each case. Reduction of the cyanolactams with LiAlH4 gave 6-amino-1,4,5,6-tetradeoxy-1,4-imino-L-lyxo-6 or -L-ribo-16-hexitol, respectively. The 6-amino-1,4,5,6-tetradeoxy-1,4-imino-L-ribo-hexitol 16 was found to be a moderate inhibitor of alpha-L-fucosidase with a K-i of 110 mu M. (C) 2000 Elsevier Science Ltd. All rights reserved.