2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-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 trichloroacetimidate | 503830-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-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 trichloroacetimidate
• 英文别名: GalNAc3Ac4Ac6Ac(b1-4)GlcNAc3Ac6Ac(b1-3)Man2Ac4Ac6Ac(b1-4)Glc2Ac3Ac6Ac(a)-O-C(NH)CCl3；[(2R,3S,4R,5R,6S)-5-acetamido-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4-acetyloxy-6-[(2R,3R,4S,5S,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxyoxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 503830-22-6
• 化学式: C₅₂H₇₀Cl₃N₃O₃₂
• 分子量: 1355.49
• InChiKey: HYBRKGSTLGVKFF-CLHJTYAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  90
• 可旋转键数：
  36
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  445
• 氢给体数：
  3
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 、 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-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 trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以40%的产率得到2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-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-...
  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-galactopyranosyl-(1->4)-2-acetamido-3,6-di-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 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 1.5h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-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 trichloroacetimidate
  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