1,2,3,6,2',3',4',6'-octa-O-pivaloyl-D-cellobiose | 865308-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,6,2',3',4',6'-octa-O-pivaloyl-D-cellobiose
• 英文别名: perpivaloylated cellobiose
• CAS: 865308-72-1
• 化学式: C₅₂H₈₆O₁₉
• 分子量: 1015.24
• InChiKey: ZDPWELNEAMHDOH-GBUPPDEGSA-N

物化性质

• 沸点：
  845.4±65.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.38
• 重原子数：
  71.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  238.09
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  1,2,3,6,2',3',4',6'-octa-O-pivaloyl-D-cellobiose 在 caesium carbonate 作用下， 生成 2,3,6,2',3',4',6'-hepta-O-pivaloyl-D-cellobiose-1-α-trichloroacetimidate
  参考文献：
  名称：

  Sugar conjugates of fulvestrant (ICI 182,780): efficient general procedures for glycosylation of the fulvestrant core

  摘要：

  We have prepared glucose and cellobiose conjugates at the phenolic 3- and hydroxylic 17-positions of the pure antiestrogenic compound fulvestrant (ICI 182,780), which has recently been approved in the USA for the treatment of advanced postmenopausal breast cancer. Glycosylation at the 17-position was achieved most effectively using pivaloyl protection of the sugar imidates employed, which we found suppressed the competing transacylation reaction and led to improved yields of the product glycosides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.140
• 作为产物：
  描述：

  三甲基乙酰氯 、 Cellobiose 以26%的产率得到1,2,3,6,2',3',4',6'-octa-O-pivaloyl-D-cellobiose
  参考文献：
  名称：

  Sugar conjugates of fulvestrant (ICI 182,780): efficient general procedures for glycosylation of the fulvestrant core

  摘要：

  We have prepared glucose and cellobiose conjugates at the phenolic 3- and hydroxylic 17-positions of the pure antiestrogenic compound fulvestrant (ICI 182,780), which has recently been approved in the USA for the treatment of advanced postmenopausal breast cancer. Glycosylation at the 17-position was achieved most effectively using pivaloyl protection of the sugar imidates employed, which we found suppressed the competing transacylation reaction and led to improved yields of the product glycosides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.140

文献信息

• Synthesis of sterically crowded derivatives of anomeric pairs of d-glucose disaccharides
  作者：Sanford Mendonca、Roger A. Laine

  DOI：10.1016/j.carres.2005.05.016

  日期：2005.9

  Derivatization of carbohydrates is of considerable interest since the derivatives can be used for structural studies in the field of mass spectrometry. We report here the synthesis of a series of sterically crowded derivatives of various linkage and stereo-isomeric glucose-glucose disaccharides with the impetus being to understand the effect of these derivatized groups on fragmentation of the glycosidic

  碳水化合物的衍生化具有相当大的意义，因为该衍生物可用于质谱领域的结构研究。我们在这里报告了一系列各种键和立体异构体葡萄糖-葡萄糖二糖的空间拥挤衍生物的合成，其推动力是了解这些衍生基团对糖苷键断裂的影响以及用于识别糖基键的方法的发展。异头配置。已经合成了全烷基化的（甲基，乙基，丙基，丁基和戊基），过酸酯化的（乙酰基，新戊酰基，甲基磺酰基）和全甲硅烷基化的（叔丁基-二甲基甲硅烷基）葡萄糖-葡萄糖二糖衍生物。报告。