1,2,3,4-tetra-O-benzyl-D-glucitol | 1316720-91-8

• 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: 1,2,3,4-tetra-O-benzyl-D-glucitol
• 英文别名: (2R,3R,4R,5S)-3,4,5,6-tetrakis(phenylmethoxy)hexane-1,2-diol
• CAS: 1316720-91-8
• 化学式: C₃₄H₃₈O₆
• 分子量: 542.672
• InChiKey: BWCSXDYPVBVIIX-KMKAFXEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-benzyl-D-glucitol 在 sodium periodate 作用下， 以 乙醚 、 水 为溶剂， 反应 24.0h， 生成 2,3:4,5-tetra-O-benzyl-L-xylose
  参考文献：
  名称：

  The synthesis of higher carbon sugars: a study on the rearrangement of higher sugar allylic alcohols

  摘要：

  The C12 higher sugar enone 15 (prepared from the corresponding phosphonate and aldehyde) was highly stereoselectively reduced to the D-glycero-allylic alcohol. The epimeric L-glycero-isomer was obtained by the non-selective reduction of the higher enone under Luche conditions. The separate treatment of both allylic alcohols with triflic anhydride provided the corresponding triflates, which in situ underwent allylic rearrangement with the elimination of one of the benzyl groups (from the aldehyde part of the molecule). The stereochemical aspects of this transformation are also discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.021
• 作为产物：
  描述：

  1,2,3,4-tetra-O-benzyl-5,6-O-isopropylidene-D-glucitol 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 以1.1 g的产率得到1,2,3,4-tetra-O-benzyl-D-glucitol
  参考文献：
  名称：

  The synthesis of higher carbon sugars: a study on the rearrangement of higher sugar allylic alcohols

  摘要：

  The C12 higher sugar enone 15 (prepared from the corresponding phosphonate and aldehyde) was highly stereoselectively reduced to the D-glycero-allylic alcohol. The epimeric L-glycero-isomer was obtained by the non-selective reduction of the higher enone under Luche conditions. The separate treatment of both allylic alcohols with triflic anhydride provided the corresponding triflates, which in situ underwent allylic rearrangement with the elimination of one of the benzyl groups (from the aldehyde part of the molecule). The stereochemical aspects of this transformation are also discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.021