2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol | 118303-61-0

• 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: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol
• 英文别名: [(E,2S,3R)-1-[(2R,3R,4S,5R,6R)-5-[(2S,3S,4S,5R,6R)-4-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-azidooctadec-4-en-3-yl] benzoate
• CAS: 118303-61-0
• 化学式: C₆₃H₉₀N₄O₂₇
• 分子量: 1335.42
• InChiKey: NWOCRBSVIWWADM-DYNIIDENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  94
• 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：
  29

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol 在 三苯基膦 作用下， 以 水 、 苯 为溶剂， 反应 24.0h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-amino-3-O-benzoyl-4-octadecene-1,3-diol
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

  摘要：

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00295-1
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 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 9.0h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

  摘要：

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00295-1