3-bromo-4-methoxyphenyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside | 319489-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromo-4-methoxyphenyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside
• CAS: 319489-46-8
• 化学式: C₅₇H₅₀BrCl₄NO₁₄
• 分子量: 1194.74
• InChiKey: HLOVKWCHSBPBRY-JCLZNRKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.38
• 重原子数：
  77.0
• 可旋转键数：
  18.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  155.98
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3-bromo-4-methoxyphenyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside 在 乙二胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Bromonium ion-promoted glycosidic bond formation and simultaneous bromination of an activated aryl aglycon

  摘要：

  N-Bromosuccinimide (NBS) together with a catalytic amount of Me3SiOTf was found to be effective for the activation of thioglycosides. Concurrently with formation of the glycosidic bond, bromination took place on the activated aromatic ring of a 4-methoxyphenyl aglycon. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00276-2
• 作为产物：
  描述：

  4-methoxyphenyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside 、 phenyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-(3,4,5,6-tetrachlorophthalimido)-β-D-thioglucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以540 mg的产率得到3-bromo-4-methoxyphenyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Bromonium ion-promoted glycosidic bond formation and simultaneous bromination of an activated aryl aglycon

  摘要：

  N-Bromosuccinimide (NBS) together with a catalytic amount of Me3SiOTf was found to be effective for the activation of thioglycosides. Concurrently with formation of the glycosidic bond, bromination took place on the activated aromatic ring of a 4-methoxyphenyl aglycon. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00276-2