2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-α-D-galactopyranosyl-(1->6)-4-O-acetyl-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside | 1064663-36-0

• 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-di-O-benzyl-α-D-galactopyranosyl-(1->6)-4-O-acetyl-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: Bn(-2)[Bn(-3)]Gal(a1-6)[Bz(-2)][Bz(-3)]Gal4Ac(a1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Gal(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Gal(b)-O-EtTMS；[(2R,3S,4S,5R,6R)-2-[[(2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5S,6R)-5-acetyloxy-3,4-dibenzoyloxy-6-[[(2S,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-3,4,5-tribenzoyloxyoxan-2-yl]oxymethyl]-4,5-dibenzoyloxy-6-(2-trimethylsilylethoxy)oxan-3-yl] benzoate
• CAS: 1064663-36-0
• 化学式: C₁₀₁H₁₀₀O₃₀Si
• 分子量: 1821.97
• InChiKey: WIYIHOFMSMGBII-IDCCQJQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.55
• 重原子数：
  132
• 可旋转键数：
  46
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  370
• 氢给体数：
  2
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-α-D-galactopyranosyl-(1->6)-4-O-acetyl-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 2-(trimethylsilyl)ethyl α-D-galactopyranosyl-(1->6)-4-O-acetyl-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of neutral glycosphingolipids from Zygomycetes

  摘要：

  Novel neutral glycosphingolipids (NGSLs) containing Gal-alpha l -> 6Gal, previously found in the Zygomycetes species Mucor hiemalis, were synthesized. The structures of these compounds are different froth those of other fungal GSLs, and they are expected to be involved in host-parasite interactions. A key step in their synthesis is direct 1,2-cis alpha-selective galactosylation of 4,6-diol tri- and tetrasaccharide acceptors with a galactosyl donor in the presence of N-iodosuccinimide (NIS)/trifluoromethane-sulfonic acid (TfOH). The fully protected glycosides were deprotected to give the two target glycosphingolipids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.019
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1->6)-4-O-acetyl-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以98.5%的产率得到2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-α-D-galactopyranosyl-(1->6)-4-O-acetyl-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of neutral glycosphingolipids from Zygomycetes

  摘要：

  Novel neutral glycosphingolipids (NGSLs) containing Gal-alpha l -> 6Gal, previously found in the Zygomycetes species Mucor hiemalis, were synthesized. The structures of these compounds are different froth those of other fungal GSLs, and they are expected to be involved in host-parasite interactions. A key step in their synthesis is direct 1,2-cis alpha-selective galactosylation of 4,6-diol tri- and tetrasaccharide acceptors with a galactosyl donor in the presence of N-iodosuccinimide (NIS)/trifluoromethane-sulfonic acid (TfOH). The fully protected glycosides were deprotected to give the two target glycosphingolipids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.019