(2S,3R,4E)-2-azido-3-benzoyloxyoctadec-4-enyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3-di-O-acetyl-6-deoxy-6-trifluoroacetamido-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 261522-54-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R,4E)-2-azido-3-benzoyloxyoctadec-4-enyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3-di-O-acetyl-6-deoxy-6-trifluoroacetamido-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: [(E,2S,3R)-2-azido-1-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4-diacetyloxy-5-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[[(2,2,2-trifluoroacetyl)amino]methyl]oxan-2-yl]oxyoxan-2-yl]oxyoctadec-4-en-3-yl] benzoate
• CAS: 261522-54-7
• 化学式: C₆₃H₈₇F₃N₄O₂₇
• 分子量: 1389.39
• InChiKey: DTOIGWMADLSGQB-DNESTJGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  97
• 可旋转键数：
  47
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  362
• 氢给体数：
  1
• 氢受体数：
  32

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-2-azido-3-benzoyloxyoctadec-4-enyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3-di-O-acetyl-6-deoxy-6-trifluoroacetamido-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 硫化氢 作用下， 以 吡啶 、 水 为溶剂， 反应 44.0h， 生成
  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 (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3-di-O-acetyl-6-deoxy-trifluoroacetamido-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 3 A molecular sieve 、 三氟化硼乙醚 、 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 3.17h， 生成 (2S,3R,4E)-2-azido-3-benzoyloxyoctadec-4-enyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3-di-O-acetyl-6-deoxy-6-trifluoroacetamido-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