11-bromoundecyl hepta-O-pivaloyl-β-lactoside | 1213234-54-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 11-bromoundecyl hepta-O-pivaloyl-β-lactoside
• CAS: 1213234-54-8
• 化学式: C₅₈H₉₉BrO₁₈
• 分子量: 1164.32
• InChiKey: IGZXMLXQMXGGAX-CZUWDKGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.71
• 重原子数：
  77.0
• 可旋转键数：
  23.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  β-乳糖 在 吡啶 、 四氯化锡 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 126.0h， 生成 11-bromoundecyl hepta-O-pivaloyl-β-lactoside
  参考文献：
  名称：

  SnCl4: An efficient and inexpensive promoter for synthesis of ω-functionalized alkyl 1,2-trans-glycosides from 1-O-pivaloyl donor

  摘要：

  SnCl4-promoted reactions of perpivaloylated lactose with various alcohols were studied in the presence or absence of an additive, CaCO3. SnCl4 was found to promote the 1,2-trans-glycosylation of alcohols in CH2Cl2 at 0A degrees C in a stereo controlled manner with beta-selectivity. The corresponding glycosides were isolated in high yields.

  DOI：

  10.1134/s1070363216010266

文献信息

• Efficient Stereoselective Glycosylations of Alcohols by Sugar Perpivalates: The First Use of 1-O-Pivaloylated Glycosyl Donors
  作者：Han Zuilhof、Aliaksei Pukin

  DOI：10.1055/s-0029-1218361

  日期：2009.12

  1-O-Pivaloyl glycosides were shown to be efficient glycosyl donors by using the perpivaloylated derivatives of lactose, galactose and glucose in the direct ZnCl2-promoted glycosylations of various alcohols. The corresponding glycosides were isolated in good yields and β-selectivity.

  在 ZnCl2 直接促进的各种醇的糖基化反应中，通过使用乳糖、半乳糖和葡萄糖的过新戊酰化衍生物，证明 1-O-Pivaloyl 糖苷是高效的糖基供体。分离出的相应糖苷具有良好的产率和δ选择性。