dimethyl (2R,3R)-2-O-(p-nitrobenzyl)tartrate | 109771-12-2

• 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: dimethyl (2R,3R)-2-O-(p-nitrobenzyl)tartrate
• 英文别名: dimethyl (2R,3R)-2-hydroxy-3-[(4-nitrophenyl)methoxy]butanedioate
• CAS: 109771-12-2
• 化学式: C₁₃H₁₅NO₈
• 分子量: 313.264
• InChiKey: TWJYXFKUKOKNGB-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl (2R,3R)-2-O-(p-nitrobenzyl)tartrate 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以82%的产率得到L-O-mono-(4-nitrobenzyl) tartaric acid
  参考文献：
  名称：

  Total Regioselective Control of Tartaric Acid

  摘要：

  An efficient strategy to synthesize tartaric acid building blocks for totally regioselective transformations or derivatizations was disclosed. Starting from L-tartaric acid or L-dimethyl tartrate, respectively, we obtained type I and II building blocks with orthogonal sets of protecing groups (4-8 steps, 38-56% overall yield).

  DOI：

  10.1021/jo101001s
• 作为产物：
  描述：

  L-(+)-酒石酸二甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 1-Butanol, tin(2+) salt 、 cesium fluoride 作用下， 以 甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以82%的产率得到dimethyl (2R,3R)-2-O-(p-nitrobenzyl)tartrate
  参考文献：
  名称：

  Total Regioselective Control of Tartaric Acid

  摘要：

  An efficient strategy to synthesize tartaric acid building blocks for totally regioselective transformations or derivatizations was disclosed. Starting from L-tartaric acid or L-dimethyl tartrate, respectively, we obtained type I and II building blocks with orthogonal sets of protecing groups (4-8 steps, 38-56% overall yield).

  DOI：

  10.1021/jo101001s

文献信息

• Selective Monoalkylation of Acyclic Diols by Means of Dibutyltin Oxide and Fluoride Salts.
  作者：Nobuo NAGASHIMA、Masaji OHNO

  DOI：10.1248/cpb.39.1972

  日期：——

  Fluoride anion was found to promote monoalkylation reaction of diols by the stannylene acetal method, and selective monoalkylation of various acyclic diols was accomplished in good yields under mild conditions by employing this new method. Functional groups such as carboxylic acid ester, carboxamide, carbamate, nitrile, alkyl chloride, and ether were not affected under the reaction conditions.

  氟化物阴离子被发现能够通过锡烯醇反应促进二醇的单烷基化反应，并且在温和条件下，采用这种新方法成功实现了多种非环状二醇的选择性单烷基化，产率良好。在反应条件下，羧酸酯、羧酰胺、氨基甲酸酯、腈、烷基氯和醚等官能团没有受到影响。
• An Efficient<i>O</i>-Monoalkylation of Dimethyl L-Tartrate via<i>O</i>-Stannylene Acetal with Alkyl Halides in the Presence of Cesium Fluoride
  作者：Nobuo Nagashima、Masaji Ohno

  DOI：10.1246/cl.1987.141

  日期：1987.1.5

  Selective O-monoalkylation of the vic-glycol of dimethyl l-tartrate with alkyl halides has been found to take place smoothly under mild conditions in the presence of cesium fluoride.

  已经发现，在氟化铯存在的温和条件下，L-酒石酸二甲酯的邻位乙二醇与卤代烷的选择性O-单烷基化反应可以顺利进行。
• NAGASHIMA NOBUO; OHNO MASAJI, CHEM. LETT.,(1987) N 1, 141-144
  作者：NAGASHIMA NOBUO、 OHNO MASAJI

  DOI：——

  日期：——
• Total Regioselective Control of Tartaric Acid
  作者：Jan Spengler、Ana I. Fernández-Llamazares、Javier Ruiz-Rodríguez、Klaus Burger、Fernando Albericio

  DOI：10.1021/jo101001s

  日期：2010.8.20

  An efficient strategy to synthesize tartaric acid building blocks for totally regioselective transformations or derivatizations was disclosed. Starting from L-tartaric acid or L-dimethyl tartrate, respectively, we obtained type I and II building blocks with orthogonal sets of protecing groups (4-8 steps, 38-56% overall yield).