3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-α-D-glucopyranosyl bromide | 180778-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-α-D-glucopyranosyl bromide
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-bromo-5-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate
• CAS: 180778-39-6
• 化学式: C₂₀H₁₆BrCl₄NO₉
• 分子量: 636.064
• InChiKey: IDKMVYIZIIGFMT-AUKCMCPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-α-D-glucopyranosyl bromide 在 盐酸 、 silver zeolite 、 水 、 四氯化钛 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Access to tetrachlorophthalimide-protected ethyl 2-amino-2-deoxy-1-thio-β-d-glucopyranosides

  摘要：

  Ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-beta-D-glucopyranoside (7) was prepared from glucosamine hydrochloride in four steps with a 20-25% overall yield. Formation of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (5) was found to be crucial for this reaction sequence since the corresponding alpha-1-acetate did not react in Lewis-acid-catalyzed ethylthio glycosidations. Formation of the beta-1-acetate (5) was achieved by treatment of 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-alpha-D-glucopyranosol bromide(4) with acetic acid under silver zeolite promotion. This was necessary because conditions normally used for p-l-acetate formation were not tolerated by the tetrachlorophthalimido (TCP) group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00309-7
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-α-D-glucopyranoside 在 氢溴酸 、 溶剂黄146 作用下， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Access to tetrachlorophthalimide-protected ethyl 2-amino-2-deoxy-1-thio-β-d-glucopyranosides

  摘要：

  Ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-beta-D-glucopyranoside (7) was prepared from glucosamine hydrochloride in four steps with a 20-25% overall yield. Formation of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (5) was found to be crucial for this reaction sequence since the corresponding alpha-1-acetate did not react in Lewis-acid-catalyzed ethylthio glycosidations. Formation of the beta-1-acetate (5) was achieved by treatment of 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-alpha-D-glucopyranosol bromide(4) with acetic acid under silver zeolite promotion. This was necessary because conditions normally used for p-l-acetate formation were not tolerated by the tetrachlorophthalimido (TCP) group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00309-7