methyl 2-O-diphenylmethyl-α-L-rhamnopyranoside | 148778-03-4

• 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: methyl 2-O-diphenylmethyl-α-L-rhamnopyranoside
• 英文别名: (2S,3R,4R,5R,6R)-5-benzhydryloxy-6-methoxy-2-methyloxane-3,4-diol
• CAS: 148778-03-4
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: PCMZDSWSJBGJBN-QHCBNBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2,3-O-(diphenylmethylene)-α-L-rhamnopyranoside 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 methyl 2-O-diphenylmethyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  A kinetic study on the reductive opening of the diphenylmethylene acetal in methyl 2,3-O-diphenylmethylene-α-l-rhamnopyranoside

  摘要：

  Reductive opening of the diphenylmethyl acetal in methyl 2,3-O-diphenylmethylene-alpha-L-rhamnopyranoside has been investigated by kinetic studies, and the results have been compared to those recently obtained by quantum chemical calculations. In contrast to the previous theoretical calculations which related only to the presumably rate limiting step of the reductive opening, the reaction system LiAlH4, AlCl3, and the title compound consists of at least four simultaneous reactions. Nevertheless, reasonable agreement can be found between the activation Gibbs free energy obtained from kinetic measurements and the theoretically calculated ones in spite of the experimental errors and the approximate nature of theoretical calculations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.041

文献信息

• A kinetic study on the reductive opening of the diphenylmethylene acetal in methyl 2,3-O-diphenylmethylene-α-l-rhamnopyranoside
  作者：Dezső Szikra、Attila Mándi、Anikó Borbás、István P. Nagy、István Komáromi、Attila Kiss-Szikszai、Mihály Herczeg、Sándor Antus

  DOI：10.1016/j.carres.2011.04.041

  日期：2011.9

  Reductive opening of the diphenylmethyl acetal in methyl 2,3-O-diphenylmethylene-alpha-L-rhamnopyranoside has been investigated by kinetic studies, and the results have been compared to those recently obtained by quantum chemical calculations. In contrast to the previous theoretical calculations which related only to the presumably rate limiting step of the reductive opening, the reaction system LiAlH4, AlCl3, and the title compound consists of at least four simultaneous reactions. Nevertheless, reasonable agreement can be found between the activation Gibbs free energy obtained from kinetic measurements and the theoretically calculated ones in spite of the experimental errors and the approximate nature of theoretical calculations. (C) 2011 Elsevier Ltd. All rights reserved.