| 1547341-67-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1547341-67-2
• 化学式: C₆₀H₇₀O₂₃
• 分子量: 1159.2
• InChiKey: BBSMYSYBPJNWAN-MNIHHTAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  83.0
• 可旋转键数：
  26.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  267.17
• 氢给体数：
  0.0
• 氢受体数：
  23.0

反应信息

• 作为产物：
  描述：

  TMS(-2)[TMS(-3)][TMS(-4)]Gal6Ac(b1-4)[TMS(-2)][TMS(-3)]Glc1Ac6Ac 在 4-二甲氨基吡啶 、 10 wt% Pd(OH)2 on carbon 、 camphor-10-sulfonic acid 、 氢气 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 、
  参考文献：
  名称：

  Integrating ReSET with Glycosyl Iodide Glycosylation in Step-Economy Syntheses of Tumor-Associated Carbohydrate Antigens and Immunogenic Glycolipids

  摘要：

  Carbohydrates mediate a wide range of biological processes, and understanding these events and how they might be influenced is a complex undertaking that requires access to pure glycoconjugates. The isolation of sufficient quantities of carbohydrates and glycolipids from biological samples remains a significant challenge that has redirected efforts toward chemical synthesis. However, progress toward complex glycoconjugate total synthesis has been slowed by the need for multiple protection and deprotection steps owing to the large number of similarly reactive hydroxyls in carbohydrates. Two methodologies, regioselective silyl exchange technology (ReSET) and glycosyl iodide glycosylation have now been integrated to streamline the synthesis of the globo series trisaccharides (globotriaose and isoglobotriaose) and alpha-lactosylceramide (alpha-LacCer). These glycoconjugates include tumor-associated carbohydrate antigens (TACAs) and immunostimulatory glycolipids that hold promise as immunotherapeutics. Beyond the utility of the step-economy syntheses afforded by this synthetic platform, the studies also reveal a unique electronic interplay between acetate and silyl ether protecting groups. Incorporation of acetates proximal to silyl ethers attenuates their reactivity while reducing undesirable side reactions. This phenomenon can be used to fine-tune the reactivity of silylated/acetylated sugar building blocks.

  DOI：

  10.1021/jo402736g