3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 26597-76-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: [(3aR,5R,6S,6aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate
• CAS: 26597-76-2
• 化学式: C₁₉H₂₄O₇
• 分子量: 364.395
• InChiKey: SGEQHRHPFTZGON-LVNYTYFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 magnesium(II) perchlorate 、 9-乙基-3,6-二甲基咔唑 作用下， 以 水 、 异丙醇 为溶剂， 反应 2.0h， 以86%的产率得到1,2:5,6-di-O-isopropylidene-3-deoxy-α-D-ribo-hexofuranose
  参考文献：
  名称：

  An Improved Photosensitizer for the Photoinduced Electron-Transfer Deoxygenation of Benzoates and m-(Trifluoromethyl)benzoates

  摘要：

  DOI：

  10.1021/jo971332y

文献信息

• SnCl4 Promoted Efficient Cleavage of Acetal/Ketal Groups with the Assistance of Water in CH2Cl2
  作者：Tao Luo、Tian-Tian Xu、Yang-Fan Guo、Hai Dong

  DOI：10.3390/molecules27238258

  日期：——

  carbohydrates containing acetal/ketal groups with the assistance of water in CH2Cl2 led to deacetalization/deketalization products in almost quantitative yields. In addition, for substrates containing both acetal/ketal and p-methoxylbenzyl groups, we also found that the p-methoxylbenzyl group was selectively cleaved by the use of a catalytic amount of SnCl4, while the acetal/ketal groups remained. Furthermore

  缩醛化和脱缩醛是一对常规操作，用于在糖基构建块的合成中保护和脱保护糖苷的 4- 和 6- 羟基。在这项研究中，我们发现在 CH2Cl2 中的水的帮助下，用含有缩醛/缩酮基团的各种碳水化合物处理 SnCl4 导致几乎定量产率的脱缩醛/脱缩酮产物。此外，对于同时含有缩醛/缩酮和对甲氧基苄基的底物，我们还发现使用催化量的 SnCl4 会选择性地裂解对甲氧基苄基，而缩醛/缩酮基团仍然存在。此外，基于此，4,6-亚苄基糖苷可以方便地转化为4,6-OAc或4-OH，6-OAc糖苷。
• A mild and efficient method for the chemoselective deprotection of acetonides with lanthanum(III) nitrate hexahydrate
  作者：S. Malla Reddy、Y. Venkat Reddy、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2005.08.081

  日期：2005.10

  Acetonides are hydrolyzed selectively and efficiently with lanthanum(111) nitrate hexahydrate in acetonitrile. The method has good compatibility with other sensitive hydroxyl protecting groups such as trityl, TBDMS, THP, OAc, OBz and OBn. (c) 2005 Elsevier Ltd. All rights reserved.
• A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO4–SiO2
  作者：Hai-Xia Liu、Qin-Pei Wu、Yi-Nan Shu、Xi Chen、Xiao-Dong Xi、Ti-Jian Du、Qing-Shan Zhang

  DOI：10.1016/j.carres.2009.08.035

  日期：2009.11

  The transformation of acetonides into acetates is frequently required in synthetic chemistry. An efficient procedure for direct conversion of acetonides into acetates in the presence of HClO4-SiO2 under mild conditions was developed. The acetonides of primary hydroxy groups are directly converted to diacetates, and the anomeric acetonides of furanosides are stereoselectively transformed into the corresponding acetyl beta-D-furanosides with a 2-acetoxyisopropyl group. (C) 2009 Elsevier Ltd. All rights reserved.