2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside | 231616-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
• CAS: 231616-56-1
• 化学式: C₇₆H₇₆O₂₅Si
• 分子量: 1417.51
• InChiKey: KMXSIMFPJHRLTA-PQTZYCIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.98
• 重原子数：
  102.0
• 可旋转键数：
  27.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  312.31
• 氢给体数：
  1.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 吡啶 作用下， 反应 3.0h， 以96%的产率得到2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis

  摘要：

  Novel neutral glycosphingolipids isolated from the metacestodes of Echinococcus multilocularis by Persat, may be expected to be involved in host-parasite interactions. We have synthesized these glycosphingolipid analogues containing 2-branched fatty alkyl residues in place of ceramide. The glycosylation of galactosyl donors 4 and 5 with each of the accepters 2 and 11 in the presence of N-iodosuccinimide (NIS)/TfOH, and the glycosylation of fucosyl donor 13 with accepters 12 and 20 in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the desired oligosaccharide derivatives at good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycosides 6, 15, 21, and 26 were converted to glycosylimidates 7, 16, 22, and 27, which were condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated give four target glycosphingolipid analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00027-0
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以82%的产率得到2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,4-di-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis

  摘要：

  Novel neutral glycosphingolipids isolated from the metacestodes of Echinococcus multilocularis by Persat, may be expected to be involved in host-parasite interactions. We have synthesized these glycosphingolipid analogues containing 2-branched fatty alkyl residues in place of ceramide. The glycosylation of galactosyl donors 4 and 5 with each of the accepters 2 and 11 in the presence of N-iodosuccinimide (NIS)/TfOH, and the glycosylation of fucosyl donor 13 with accepters 12 and 20 in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the desired oligosaccharide derivatives at good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycosides 6, 15, 21, and 26 were converted to glycosylimidates 7, 16, 22, and 27, which were condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated give four target glycosphingolipid analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00027-0