(3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate | 261522-51-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
• CAS: 261522-51-4
• 化学式: C₄₀H₅₀Cl₃F₃N₂O₂₅
• 分子量: 1122.19
• InChiKey: YXMDOCMIDWRJQV-ZESZQBFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.62
• 重原子数：
  73.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  345.03
• 氢给体数：
  2.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 、 (3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate 在 3 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以65%的产率得到(2S,3R,4E)-2-azido-3-benzoyloxyoctadec-4-enyl (3,4,6,tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of selected aminodeoxy analogs of globotriosylceramide

  摘要：

  Four aminodeoxy analogs of globotriosylceramide (6 "-, 4 "-, 2 "'-, and 6'-aminodeoxy) were synthesized by glycosylation of 3-O-benzoylated azidosphingosine with the corresponding aminodeoxy-globotriose trichloroacetimidate, followed by reduction of the azido group: N-acylation with 1-adamantaneacetic acid, and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00231-1
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranossyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 (3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of selected aminodeoxy analogs of globotriosylceramide

  摘要：

  Four aminodeoxy analogs of globotriosylceramide (6 "-, 4 "-, 2 "'-, and 6'-aminodeoxy) were synthesized by glycosylation of 3-O-benzoylated azidosphingosine with the corresponding aminodeoxy-globotriose trichloroacetimidate, followed by reduction of the azido group: N-acylation with 1-adamantaneacetic acid, and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00231-1