2-(trimethylsilyl)ethyl α-D-mannopyranoside | 81336-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl α-D-mannopyranoside
• 英文别名: 2-(Trimethylsilyl)ethyl-α-D-mannopyranosid；(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxane-3,4,5-triol
• CAS: 81336-89-2
• 化学式: C₁₁H₂₄O₆Si
• 分子量: 280.393
• InChiKey: UZUSRQONJTXSJN-UVOCVTCTSA-N

物化性质

• 沸点：
  411.6±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.86
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(Trimethylsilyl)ethyl-<2,3,4-tri-O-benzyl-6-0-methyl-α-D-mannopyranosid>
  参考文献：
  名称：

  Paulsen, Hans; Pries, Meike; Lorentzen, Jens Peter, Liebigs Annalen der Chemie, 1994, # 4, p. 389 - 398

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(Trimethylsilyl)ethyl-<2,3,4,6-tetra-O-acetyl-α-D-mannopyranosid> 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以96%的产率得到2-(trimethylsilyl)ethyl α-D-mannopyranoside
  参考文献：
  名称：

  Paulsen, Hans; Pries, Meike; Lorentzen, Jens Peter, Liebigs Annalen der Chemie, 1994, # 4, p. 389 - 398

  摘要：

  DOI：

文献信息

• Synthetic Study onCampylobacter jejuni Lipopolysaccharides: An Improved Synthesis of a Branched, Heptose-Containing Trisaccharide Core Structure and Its Conversion into Ganglioside GD3 Related Hexasaccharide
  作者：Koji Hori、Naoki Sawada、Hiromune Ando、Hideharu Ishida、Makoto Kiso

  DOI：10.1002/ejoc.200300309

  日期：2003.10

  The first synthesis of the oligosaccharide skeleton of the Campylobacter jejuni lipooligosaccharide composed of a branched, heptose-containing trisaccharide core structure and, including a substantially improved preparation of the core structure, the ganglioside GD3 related trisaccharide epitope is reported. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  首次合成空肠弯曲杆菌脂寡糖的寡糖骨架，由支链、含庚糖的三糖核心结构组成，包括核心结构的大幅改进制备，与神经节苷脂 GD3 相关的三糖表位。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• A synthesis of 2-(trimethylsilyl)ethyl α-D-mannopyranoside
  作者：Vince Pozsgay

  DOI：10.1016/s0040-4039(00)79280-x

  日期：1993.11

  The first high yield synthesis is reported of 2-(trimethylsilyl)ethyl α-D-mannopyranoside using 2-O-benzoylated mannosyl donors, as precursors.

  报道了使用2- O-苯甲酰化的甘露糖基供体作为前体的2-（三甲基甲硅烷基）乙基α-D-甘露吡喃糖苷的首次高产率合成。
• Probing the Substrate Specificity of Golgi α-Mannosidase II by Use of Synthetic Oligosaccharides and a Catalytic Nucleophile Mutant
  作者：Wei Zhong、Douglas A. Kuntz、Brian Ember、Harminder Singh、Kelley W. Moremen、David R. Rose、Geert-Jan Boons

  DOI：10.1021/ja711248y

  日期：2008.7.1

  provides a route to blocking cancer-induced changes in cell surface oligosaccharide structures. To probe the substrate requirements of GMII, oligosaccharides were synthesized that contained an alpha(1,3)- or alpha(1,6)-linked 1-thiomannoside. Surprisingly, these oligosaccharides were not observed in X-ray crystal structures of native Drosophila GMII (dGMII). However, a mutant enzyme in which the catalytic

  抑制高尔基体 α-甘露糖苷酶 II (GMII)，它在 N-聚糖加工途径的后期起作用，提供了阻断癌症诱导的细胞表面寡糖结构变化的途径。为了探测 GMII 的底物要求，合成了含有 alpha(1,3)-或 alpha(1,6)-连接的 1-thiomannoside 的寡糖。令人惊讶的是，在天然果蝇 GMII (dGMII) 的 X 射线晶体结构中没有观察到这些寡糖。然而，其中催化亲核天冬氨酸变为丙氨酸 (D204A) 的突变酶允许浸泡低聚糖的可视化，并导致鉴定天然底物的 α(1,3) 连接甘露糖苷的结合位点。这些研究还表明，结合的甘露糖苷的构象变化为高能 B 2，Asp2O4 的空间位阻和强氢键的形成促进了 Asp2O4 的 5 构象。观察到 dGMII 的催化位点不能很好地耐受 1-硫连接的甘露糖苷，导致合成了一种五糖，其中包含天然底物的 α(1,6)-连接的 Man 和β(1,2)-连接的
• Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems
  作者：Alison M. Daines、Ben W. Greatrex、Colin M. Hayman、Sarah M. Hook、Warren T. McBurney、Thomas Rades、Phillip M. Rendle、Ian M. Sims

  DOI：10.1016/j.bmc.2009.05.043

  日期：2009.7

  Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed. (C) 2009 Elsevier Ltd. All rights reserved.