3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-α-D-glucopyranosyl trichloroacetimidate | 904319-35-3

• 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-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Fuc2Ac3Ac4Ac(a1-3)[Bz(-2)Man3Ac4Ac6Ac(b1-4)][Bz(-2)]Glc6Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-6-(acetyloxymethyl)-5-[(2S,3S,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-benzoyloxyoxan-2-yl]oxy-4-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 904319-35-3
• 化学式: C₄₈H₅₄Cl₃NO₂₄
• 分子量: 1135.31
• InChiKey: MDKXPCAAOXHYCF-HLLMSSESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  76
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  316
• 氢给体数：
  1
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-α-D-glucopyranosyl trichloroacetimidate 在 molecular sieve 、 三氟甲磺酸三甲基硅酯 、 溶剂黄146 、 三乙胺 、 焦碳酸二乙酯 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Synthesis of a novel glycosphingolipid from the millipede, Parafontaria laminata armigera, and the assembly of its carbohydrate moiety into multivalent structures

  摘要：

  A novel glycosphingolipid, beta-D-Manp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-Glcp-(1 -> 1)-Cer, found in the millipede, Parafontaria laminata armigera, and multivalent derivatives of its carbohydrate moiety were synthesized. As the key step, the target glycolipid (1) was obtained through an inversion reaction at the 2-position of a beta-glucopyranoside residue yielding a P-mannopyranoside. In addition, the synthesis of fluorescently labeled trimer and tetramer glycoconjugates (2, 3) was achieved by iterative amide bond formation using a monomer unit (24). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.019
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-β-D-glucopyranoside 、 三氯乙腈 在 三氟乙酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以86%的产率得到3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of a novel glycosphingolipid from the millipede, Parafontaria laminata armigera, and the assembly of its carbohydrate moiety into multivalent structures

  摘要：

  A novel glycosphingolipid, beta-D-Manp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-Glcp-(1 -> 1)-Cer, found in the millipede, Parafontaria laminata armigera, and multivalent derivatives of its carbohydrate moiety were synthesized. As the key step, the target glycolipid (1) was obtained through an inversion reaction at the 2-position of a beta-glucopyranoside residue yielding a P-mannopyranoside. In addition, the synthesis of fluorescently labeled trimer and tetramer glycoconjugates (2, 3) was achieved by iterative amide bond formation using a monomer unit (24). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.019