3-acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam | 1167984-87-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam
• 英文别名: N-[(2R,3R,4S,5R)-3,5-dihydroxy-2-methyl-6-oxopiperidin-4-yl]acetamide
• CAS: 1167984-87-3
• 化学式: C₈H₁₄N₂O₄
• 分子量: 202.21
• InChiKey: YHCBDVNINNFGHR-VYNVVFCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam 、 乙酸酐 在 吡啶 作用下， 生成 3-acetamido-2,4-di-O-acetyl-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam
  参考文献：
  名称：

  A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-d-glucitol

  摘要：

  3-Acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-D-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-beta-D-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.016
• 作为产物：
  描述：

  methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-D-xylo-hex-5-ulosonate oxime 在 palladium on activated charcoal 、 氢气 、 sodium methylate 作用下， 以 溶剂黄146 、 甲醇 为溶剂， 55.0 ℃ 、5.0 MPa 条件下， 反应 49.0h， 以57%的产率得到3-acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam
  参考文献：
  名称：

  A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-d-glucitol

  摘要：

  3-Acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-D-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-beta-D-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.016