2-(Trimethylsilyl)ethyl 2-azido-2-deoxy-3,4-isopropylidene-β-D-galactopyranoside | 151651-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2-(Trimethylsilyl)ethyl 2-azido-2-deoxy-3,4-isopropylidene-β-D-galactopyranoside
• 英文别名: [(3aR,4R,6R,7R,7aR)-7-azido-2,2-dimethyl-6-(2-trimethylsilylethoxy)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methanol
• CAS: 151651-21-7
• 化学式: C₁₄H₂₇N₃O₅Si
• 分子量: 345.471
• InChiKey: NKNQUJLKHBRTIP-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 2-(Trimethylsilyl)ethyl 2-azido-2-deoxy-3,4-isopropylidene-β-D-galactopyranoside 在 吡啶 作用下， 反应 1.0h， 生成 Benzoic acid (3aR,4R,6R,7R,7aR)-7-azido-2,2-dimethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester
  参考文献：
  名称：

  Synthesis of Ganglioside Lactams Corresponding to GM1-, GM2-, GM3-, and GM4-Ganglioside Lactones

  摘要：

  Ganglioside lactams are potentially useful analogs of ganglioside lactones, which are highly immunogenic derivatives of gangliosides. The lactam corresponding to the G(M3)-lactone saccharide has been synthesized by sialylation of a suitably protected lactose derivative carrying an azido group in the 2'-position, followed by reduction and ring closure to form G(M3)-lactam. Glycosylation in the 4-position of the central saccharide unit gave the G(M2)- and G(M1)- lactam saccharides. By a similar route, a 2-azido-Gal derivative was sialylated and treated as above to give the G(M4)-lactam saccharide. Deprotection gave the G(M2-4)-lactam saccharides in water soluble form, whereas attempted deprotection of the G(M1)-lactam caused its degradation. The G(M3)-lactam saccharide was coupled to ceramide, to afford the ganglioside lactam analog, and via a spacer to bovine serum albumin (BSA). The BSA conjugate was used as immunogen to raise monoclonal antibodies that cross-reacted with G(M3)-lactone. The antibodies were used in a histological staining of murine melanoma cells, clearly showing the presence of G(M3)-lactone on the cell surface. Keeping the G(M2-4)-lactam saccharides in D2O at 37 degrees C for 1 month caused marginal (0-11%) hydrolysis of the lactam ring.

  DOI：

  10.1021/ja00122a002
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2-azido-2-deoxy-β-D-galactopyranoside 在 三乙胺 作用下， 以 甲醇 、 对甲苯磺酸 、 2,2-二甲氧基丙烷 、 甲苯 为溶剂， 以86%的产率得到2-(Trimethylsilyl)ethyl 2-azido-2-deoxy-3,4-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Ganglioside analogs

  摘要：

  通用公式(I)的神经节苷脂内酰胺类似物衍生物，其中A是通过虚线连接到2位的公式(II)的唾液酸残基；Z.sup.1是—OH或—NHX.sup.1基团，Y.sup.30是—CH.sub.3或—CH.sub.2OH；X.sup.1和Y.sup.1共同形成键，Y.sup.2是—OH或—OR.sup.20基团，或者X.sup.1和Y.sup.2共同形成键，Y.sup.1是—OH或—NHAc；Y.sup.3是—OH或—OR.sup.20基团；R.sup.1是H或通过虚线连接到2位的公式(III)的唾液酸残基；Z.sup.2是—OH或—NHX.sup.2基团，Y.sup.30如上定义；X.sup.2和Y.sup.10共同形成键，Y.sup.20是—OH，或者X.sup.2和Y.sup.20共同形成键，Y.sup.10是—OH；但是当R.sup.1是H时，Z.sup.1是—NHX.sup.1，当R.sup.1是公式(III)的唾液酸残基时，至少一个Z.sup.1和Z.sup.2不同于—OH；R.sup.10是H，载体CA，或者基团-(糖)n。这些化合物是水解稳定的内酰胺类似物，空间上与自然发生的神经节苷脂内酯非常相似，具有抗原性，并能诱导产生与相应的神经节苷脂内酯发生交叉反应的抗体。

  公开号：

  US05637569A1