dodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-O-acetyl-β-D-galactopyranosyl-(1->6)-3,4-isopropylidene-β-D-galactopyranoside | 263247-11-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-O-acetyl-β-D-galactopyranosyl-(1->6)-3,4-isopropylidene-β-D-galactopyranoside
• CAS: 263247-11-6
• 化学式: C₄₇H₇₄O₂₃
• 分子量: 1007.09
• InChiKey: HNWWVJDFMQYPDU-KUTBBIGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  70.0
• 可旋转键数：
  26.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  278.17
• 氢给体数：
  1.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate 、 dodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-O-acetyl-β-D-galactopyranosyl-(1->6)-3,4-isopropylidene-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到dodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-[2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)]-3,4-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a tetrasaccharide representing a minimal epitope of an arabinogalactan

  摘要：

  The hydrophobic alkyl chain-containing tetrasaccharide, dodecyl beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranosyl-(1-->6)-[alpha-L - arabinofuranosyl-(1-->2)]-beta-D-galactopyranoside, was synthesized efficiently using a convergent strategy. In coupling reactions, protected trichloroacetimidates proved to be better donors than their corresponding bromides in the preparation of the dodecyl disaccharide and trisaccharide. Zemplén deacylation provided the target tetramer in good overall yield.

  DOI：

  10.1016/s0008-6215(99)00252-9
• 作为产物：
  描述：

  dodecyl β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 17.0h， 生成 dodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-O-acetyl-β-D-galactopyranosyl-(1->6)-3,4-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a tetrasaccharide representing a minimal epitope of an arabinogalactan

  摘要：

  The hydrophobic alkyl chain-containing tetrasaccharide, dodecyl beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranosyl-(1-->6)-[alpha-L - arabinofuranosyl-(1-->2)]-beta-D-galactopyranoside, was synthesized efficiently using a convergent strategy. In coupling reactions, protected trichloroacetimidates proved to be better donors than their corresponding bromides in the preparation of the dodecyl disaccharide and trisaccharide. Zemplén deacylation provided the target tetramer in good overall yield.

  DOI：

  10.1016/s0008-6215(99)00252-9