(1S,2R)-1-((2R,3R,4S)-3-acetamido-4-acetoxy-6-(methoxycarbonyl)-6-(((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate | 345209-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-acetoxy-6-(methoxycarbonyl)-6-(((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
• CAS: 345209-46-3
• 化学式: C₄₈H₅₉NO₁₈
• 分子量: 937.992
• InChiKey: BOUWOVPSJSQLNM-YUKMITJQSA-N

物化性质

• 沸点：
  912.6±65.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  67.0
• 可旋转键数：
  22.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  225.21
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosate 在 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-acetoxy-6-(methoxycarbonyl)-6-(((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
  参考文献：
  名称：

  Efficient sialylation with phosphite as leaving group

  摘要：

  DOI：

  10.1016/s0040-4039(00)60022-9

文献信息

• An Effective Sialylation Method Using<i>N</i>-Troc- and<i>N</i>-Fmoc-protected β-Thiophenyl Sialosides and Application to the One-pot Two-step Synthesis of 2,6-Sialyl-T Antigen
  作者：Takashi Takahashi、Masaatsu Adachi、Hiroshi Tanaka

  DOI：10.1055/s-2004-817759

  日期：——

  We describe an efficient sialylation method using β-thiosialosides with various N-protecting groups. Modification of the C-5 amino group of β-thiosialosides into N-Fmoc and N-Troc derivatives enhanced their reactivity in glycosidation. In addition, a minimum amount of MS-3 A was effective to improve the yield of α-linked sialoside. Branched type one-pot glycosylation initiating glycosidation of the

  我们描述了一种使用具有各种 N 保护基团的 β-硫代唾液酸的有效唾液酸化方法。将 β-硫代唾液酸苷的 C-5 氨基修饰为 N-Fmoc 和 N-Troc 衍生物增强了它们在糖苷化中的反应性。此外，最少量的 MS-3 A 可有效提高 α-连接的唾液酸苷的产率。支链型一锅糖基化在伯醇处启动 N-Troc 保护的 β-噻吩唾液酸苷的糖苷化，以良好的产率提供受保护的 2,6-唾液酸-T 抗原，将其转化为完全脱保护的糖基氨基酸。
• Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism
  作者：Hirosato Kondo、Shin Aoki、Yoshitaka Ichikawa、Randall L. Halcomb、Helena Ritzen、Chi-Huey Wong

  DOI：10.1021/jo00083a032

  日期：1994.2

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.