methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-D-xylo-hex-5-ulosonate | 1167984-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-D-xylo-hex-5-ulosonate
• CAS: 1167984-83-9
• 化学式: C₁₅H₂₁NO₁₀
• 分子量: 375.332
• InChiKey: CNNFJAZYHAOZHG-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.34
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  151.37
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-D-xylo-hex-5-ulosonate 在 吡啶 、 盐酸羟胺 作用下， 生成 methyl (2R,3S,4S,5Z)-3-acetamido-2,4,6-triacetyloxy-5-hydroxyiminohexanoate 、
  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-β-D-ribohexapyranoside 在 chromium(VI) oxide 、 乙酸酐 、 溶剂黄146 作用下， 反应 2.0h， 以85%的产率得到methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-D-xylo-hex-5-ulosonate
  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