2-(trimethylsilyl)ethyl (2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 260976-45-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(trimethylsilyl)ethyl (2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-6)]Gal(b1-4)[Bz(-2)][Bz(-3)][Bz(-6)]Glc(b)-O-EtTMS；[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-6-[(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-3-hydroxyoxan-2-yl]methyl benzoate
• CAS: 260976-45-2
• 化学式: C₅₉H₅₈O₁₇Si
• 分子量: 1067.18
• InChiKey: NPGFQMKJQKWURX-RBQCBCIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.15
• 重原子数：
  77
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-galactopyranosside 、 2-(trimethylsilyl)ethyl (2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以94%的产率得到2-(trimethylsilyl)ethyl (2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of selected aminodeoxy analogues of galabiose and globotriose

  摘要：

  Six aminodeoxy 2-(trimethylsilyl)ethyl (Me3SiEt) glycoside analogues of galabiose (4'- and 6'-aminodeoxy) and globotriose (6 "-, 4 "-, 2 "-, and 6'-aminodeoxy) were synthesized by glycosylation of protected Me3SiEt galactoside and lactoside accepters with azido-substituted monosaccharide donors, followed by reduction of the azido groups and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00229-3
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (2,3-di-O-benzoyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl)-(->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 吡啶 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 6.5h， 生成 2-(trimethylsilyl)ethyl (2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of selected aminodeoxy analogues of galabiose and globotriose

  摘要：

  Six aminodeoxy 2-(trimethylsilyl)ethyl (Me3SiEt) glycoside analogues of galabiose (4'- and 6'-aminodeoxy) and globotriose (6 "-, 4 "-, 2 "-, and 6'-aminodeoxy) were synthesized by glycosylation of protected Me3SiEt galactoside and lactoside accepters with azido-substituted monosaccharide donors, followed by reduction of the azido groups and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00229-3

文献信息

• Analogues of Glycosphingolipids and Glycerolipids Suitable for Conjugation to Gold- and Amino-Functionalised Surfaces
  作者：Jörgen Ohlsson、Göran Magnusson

  DOI：10.1016/s0040-4020(00)00946-7

  日期：2000.12

  A general synthesis of analogues of natural lipids, (i.e. lactosylceramide, globotriasylceramide, and phosphatidylcholine) where one of the alkyl chains carries a terminal thiol- or carboxyl functionality, is described. The lipids were prepared by N- or O-acylation of sphingosine or monoacylglycerol derivatives. These lipids are suitable for anchoring to gold- or amino-functionalised surfaces, thus

  描述了天然脂类似物（即乳糖基神经酰胺，globoriasyl神经酰胺和磷脂酰胆碱）的类似物的一般合成，其中烷基链之一带有末端硫醇或羧基官能团。通过鞘氨醇或单酰基甘油衍生物的N-或O-酰化制备脂质。这些脂质适用于锚定在金或氨基官能化的表面，从而形成细胞膜的模拟物，用于研究蛋白质与碳水化合物的相互作用。