2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]-1,2-benzoselenazol-3-one | 1259999-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]-1,2-benzoselenazol-3-one
• CAS: 1259999-60-4
• 化学式: C₁₄H₁₇NO₆Se
• 分子量: 374.252
• InChiKey: YPNBIEUCZRCGAF-MNNAQAQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.32
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.5
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-methoxy-5-(3-oxo-1,2-benzoselenazol-2-yl)oxan-2-yl]methyl acetate 在 甲醇 、 sodium methylate 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以93%的产率得到2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]-1,2-benzoselenazol-3-one
  参考文献：
  名称：

  Synthesis of D-Glucosamine-Modified Benzo[d][1,2]selenazol-3-(2H)-one Derivatives

  摘要：

  A new class of organoselenium-saccharide derivatives, 2-amino-2-deoxy--D-glucose-modified benzo[d][1,2]selenazol-3-(2H)-one derivatives, has been synthesized via the cyclization reaction of 2-(chloroseleno)benzoyl chloride and O-protected D-glucosamine derivatives. An efficient synthetic method for the preparation of this type of compounds was developed. It has been found that acetone can react with the chloroseleno group under basic conditions, and organoselenium-saccharide derivatives with free hydroxy groups were obtained only when the OH-1 group of the saccharide was protected.

  DOI：

  10.1080/00397910903434562

文献信息

• Synthesis of D-Glucosamine-Modified Benzo[<i>d</i>][1,2]selenazol-3-(<i>2H</i>)-one Derivatives
  作者：Zhongwei Zhang、Sumei Ren、Shengbiao Wan、Wei Li、Tao Jiang

  DOI：10.1080/00397910903434562

  日期：2010.11.3

  A new class of organoselenium-saccharide derivatives, 2-amino-2-deoxy--D-glucose-modified benzo[d][1,2]selenazol-3-(2H)-one derivatives, has been synthesized via the cyclization reaction of 2-(chloroseleno)benzoyl chloride and O-protected D-glucosamine derivatives. An efficient synthetic method for the preparation of this type of compounds was developed. It has been found that acetone can react with the chloroseleno group under basic conditions, and organoselenium-saccharide derivatives with free hydroxy groups were obtained only when the OH-1 group of the saccharide was protected.