dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside | 263247-10-5

• 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 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside
• 英文别名: [(2S,3S,4R,5S)-5-[[(3aS,4R,6R,7R,7aS)-6-dodecoxy-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 263247-10-5
• 化学式: C₄₇H₆₀O₁₃
• 分子量: 832.986
• InChiKey: RCUKIDBSNMEMHZ-VBUHURGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  60
• 可旋转键数：
  25
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate 、 dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-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91%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 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 38.0h， 生成 dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-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

文献信息

• Synthesis of a tetrasaccharide representing a minimal epitope of an arabinogalactan
  作者：Yuguo Du、Qingfeng Pan、Fanzuo Kong

  DOI：10.1016/s0008-6215(99)00252-9

  日期：1999.1

  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.