1-hexyl 2-acetamido-4,6-O-benzylidene-3-O-<2-(4-<4-phenyl>butanamido)ethyl>-2-deoxy-β-D-glucopyranoside | 231607-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-hexyl 2-acetamido-4,6-O-benzylidene-3-O-<2-(4-<4-phenyl>butanamido)ethyl>-2-deoxy-β-D-glucopyranoside
• CAS: 231607-27-5
• 化学式: C₃₇H₅₃Cl₂N₃O₇
• 分子量: 722.75
• InChiKey: CSNOYNHZKUSYFD-WTHBACDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  49.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  107.59
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-hexyl 2-acetamido-4,6-O-benzylidene-3-O-<2-(4-<4-phenyl>butanamido)ethyl>-2-deoxy-β-D-glucopyranoside 在 盐酸 、 Amberlite IRA-440C (OH^- form) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到1-hexyl 2-acetamido-3-O-<2-(4-<4-phenyl>butanamido)ethyl>-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Alkylating agents from sugars. Alkyl hexopyranoside derivatives as carrier systems for chlorambucil

  摘要：

  Chlorambucil derivatives involving alkyl 2-aminodeoxy sugars have been synthesized in good yield by coupling the chlorambucil moiety to positions C-2 or C-3 of the sugar, directly or via a spacer. The starting material was easily available from 2-acetamido-2-deoxy-D-glucose. The final compounds were tested for cytotoxicity, and some of those that presented the best results were studied for inhibition of cell proliferation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00030-0
• 作为产物：
  描述：

  1-hexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 cobalt(II) chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 1-hexyl 2-acetamido-4,6-O-benzylidene-3-O-<2-(4-<4-phenyl>butanamido)ethyl>-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Alkylating agents from sugars. Alkyl hexopyranoside derivatives as carrier systems for chlorambucil

  摘要：

  Chlorambucil derivatives involving alkyl 2-aminodeoxy sugars have been synthesized in good yield by coupling the chlorambucil moiety to positions C-2 or C-3 of the sugar, directly or via a spacer. The starting material was easily available from 2-acetamido-2-deoxy-D-glucose. The final compounds were tested for cytotoxicity, and some of those that presented the best results were studied for inhibition of cell proliferation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00030-0