diethyl (2RS,3RS)-2-hydroxy-3-(4-methylphenylsulfonyloxy)butane-1,4-dioate

• 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: diethyl (2RS,3RS)-2-hydroxy-3-(4-methylphenylsulfonyloxy)butane-1,4-dioate
• 英文别名: diethyl tartrate mono(tosylate)；diethyl (2S,3S)-2-hydroxy-3-(4-methylphenyl)sulfonyloxybutanedioate
• 化学式: C₁₅H₂₀O₈S
• 分子量: 360.385
• InChiKey: CNLOWGMSIACIFE-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl (2RS,3RS)-2-hydroxy-3-(4-methylphenylsulfonyloxy)butane-1,4-dioate 在 sodium hydroxide 、 phosphate buffer 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 ethyl 2-methylpropyl (2S,3S)-2-hydroxy-3-(4-methylphenylsulfonyloxy)butane-1,4-dioate
  参考文献：
  名称：

  Crout, David H. G.; Gaudet, S. B.; Hallinan, Keith O., Journal of the Chemical Society. Perkin transactions I, 1993, # 7, p. 805 - 812

  摘要：

  DOI：
• 作为产物：
  描述：

  D-(-)-酒石酸二乙酯 、 对甲苯磺酰氯 在 二正丁基氧化锡 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.42h， 以65%的产率得到diethyl (2RS,3RS)-2-hydroxy-3-(4-methylphenylsulfonyloxy)butane-1,4-dioate
  参考文献：
  名称：

  Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols:  Scope and Mechanistic Insight

  摘要：

  This paper describes a convenient protocol for the regioselective sulfonylation of alpha-chelatable alcohols. Typically, the reaction of alpha-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of Sn-119 NMR studies.

  DOI：

  10.1021/ja016031r

文献信息

• Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols:  Scope and Mechanistic Insight
  作者：Michael J. Martinelli、Rajappa Vaidyanathan、Joseph M. Pawlak、Naresh K. Nayyar、Ulhas P. Dhokte、Christopher W. Doecke、Lisa M. H. Zollars、Eric D. Moher、Vien Van Khau、Berta Košmrlj

  DOI：10.1021/ja016031r

  日期：2002.4.1

  This paper describes a convenient protocol for the regioselective sulfonylation of alpha-chelatable alcohols. Typically, the reaction of alpha-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of Sn-119 NMR studies.
• Crout, David H. G.; Gaudet, S. B.; Hallinan, Keith O., Journal of the Chemical Society. Perkin transactions I, 1993, # 7, p. 805 - 812
  作者：Crout, David H. G.、Gaudet, S. B.、Hallinan, Keith O.

  DOI：——

  日期：——