2-(trimethylsilyl)ethyl (2,3-di-O-acetyl-4,6-benzylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 152883-50-6

• 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-di-O-acetyl-4,6-benzylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3-[[(2S,4aR,6S,7R,8S,8aS)-7,8-diacetyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-4,5-diacetyloxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl acetate
• CAS: 152883-50-6
• 化学式: C₃₄H₄₈O₁₆Si
• 分子量: 740.831
• InChiKey: HMJAVUITIMYYHC-CFKUGKMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  51
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  187
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (2,3-di-O-acetyl-4,6-benzylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 溶剂黄146 作用下， 反应 9.0h， 以86%的产率得到2-(trimethylsilyl)ethyl (2,3-di-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  S-Linked Ganglioside Analogues for Use in Conjugate Vaccines

  摘要：

  Glycosidase resistant thioglycoside precursors of the melanoma-associated ganglioside GM(2) have been synthesized starting from lactose. Syntheses of several analogues of ganglioside GM(3) and a positional isomer have been developed. These compounds contain thio-linked sialic acid residues and a modified ceramide aglycon functionalized for coupling to proteins, surfaces, or matrices. The hydrolytic stability of these oligosaccharides enhances the immunogenicity of the corresponding conjugate vaccines by ensuring their integrity in the acidic compartments of antigen processing cells.

  DOI：

  10.1021/ol036460p
• 作为产物：
  描述：

  乙酸酐 、 (4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R)-4,5-Dihydroxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 在 吡啶 作用下， 以84%的产率得到2-(trimethylsilyl)ethyl (2,3-di-O-acetyl-4,6-benzylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  S-Linked Ganglioside Analogues for Use in Conjugate Vaccines

  摘要：

  Glycosidase resistant thioglycoside precursors of the melanoma-associated ganglioside GM(2) have been synthesized starting from lactose. Syntheses of several analogues of ganglioside GM(3) and a positional isomer have been developed. These compounds contain thio-linked sialic acid residues and a modified ceramide aglycon functionalized for coupling to proteins, surfaces, or matrices. The hydrolytic stability of these oligosaccharides enhances the immunogenicity of the corresponding conjugate vaccines by ensuring their integrity in the acidic compartments of antigen processing cells.

  DOI：

  10.1021/ol036460p

文献信息

• Mild and efficient method for the cleavage of benzylidene acetals using HClO4–SiO2 and direct conversion of acetals to acetates
  作者：Geetanjali Agnihotri、Anup Kumar Misra

  DOI：10.1016/j.tetlet.2006.03.133

  日期：2006.5

  HClO4–SiO2 has been used successfully for the deprotection of benzylidene acetals and the direct conversion of benzylidene acetals to the corresponding di-O-acetates. The reactions are very fast and yields are excellent.

  HClO 4 -SiO 2已成功用于亚苄基乙缩醛的脱保护和将亚苄基乙缩醛直接转化为相应的二-O-乙酸酯。反应非常快，收率非常好。
• Synthesis of the monodeoxy derivatives of 2-(trimethylsilyl)ethyl β-lactoside
  作者：Tomas Ekberg、Göran Magnusson

  DOI：10.1016/0008-6215(93)84028-5

  日期：1993.8

  Monodeoxy derivatives of 2-(trimethylsilyl)ethyl (Me3SiEt) beta-lactoside were synthesized, by deoxygenation at the disaccharide level, for the 2'-, 3'-, 4'-, and 6'-monodeoxylactosides. The 2-, 3-, and 6-deoxy derivatives were synthesized by beta-D-galactosylation of suitably protected monodeoxygenated Me3SiEt glucosides. Silver silicate was shown to be an efficient glycosylation promoter in the preparation

  通过在二糖水平上脱氧，合成2-（三甲基甲硅烷基）乙基（Me 3 SiEt）β-乳糖苷的单脱氧衍生物，用于2'-，3'-，4'-和6'-单脱氧乳糖苷。通过适当保护的单脱氧Me3SiEt葡糖苷的β-D-半乳糖基化合成2-，3-和6-脱氧衍生物。在制备2-和3-脱氧乳糖苷中，硅酸银被证明是有效的糖基化促进剂。