[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-(12-bromododecoxy)oxan-2-yl]methyl benzoate | 1038587-88-0

• 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: [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-(12-bromododecoxy)oxan-2-yl]methyl benzoate
• CAS: 1038587-88-0
• 化学式: C₄₆H₅₁BrO₁₀
• 分子量: 843.809
• InChiKey: QUNXFJARLBCYNJ-UTRBWMKUSA-N

物化性质

• 沸点：
  846.1±65.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  57
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  12-溴-1-十二烷醇 、 Α-D-五苯甲酸酰吡喃葡萄糖 在 六甲基二硅烷 、 碘 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 以82%的产率得到12-bromododecyl-tetra-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters

  摘要：

  Reactions of O-benzoylated glucopyranosyl halide (I, Br), isolated or generated in situ from per-benzoylated glucose (8a) and trimethylsilyl halide, with various alcohols were efficiently promoted by zinc halide (Cl, Br) or N-bromosuccinimide with a catalytic ZnI2 to give the corresponding 1,2- trans-beta-glucosides in good to high yields. When the anomeric halogenation of 8a was carried out in the presence of reactive alcohols, 1,2-cis-alpha-glucosides were selectively formed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.03.019

文献信息

• Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters
  作者：Teiichi Murakami、Yukari Sato、Motonari Shibakami

  DOI：10.1016/j.carres.2008.03.019

  日期：2008.6

  Reactions of O-benzoylated glucopyranosyl halide (I, Br), isolated or generated in situ from per-benzoylated glucose (8a) and trimethylsilyl halide, with various alcohols were efficiently promoted by zinc halide (Cl, Br) or N-bromosuccinimide with a catalytic ZnI2 to give the corresponding 1,2- trans-beta-glucosides in good to high yields. When the anomeric halogenation of 8a was carried out in the presence of reactive alcohols, 1,2-cis-alpha-glucosides were selectively formed. (C) 2008 Elsevier Ltd. All rights reserved.