(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid monomethyl ester | 263550-15-8

• 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: (4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid monomethyl ester
• 英文别名: (4R,5R)-5-methoxycarbonyl-2-phenyl-1,3-dioxolane-4-carboxylic acid
• CAS: 263550-15-8
• 化学式: C₁₂H₁₂O₆
• 分子量: 252.224
• InChiKey: SSWIRGPYEQJMDN-LSLJNABFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid monomethyl ester 在 lithium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 47.0h， 生成 (4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]
  参考文献：
  名称：

  几丁质合酶抑制剂C-糖基核苷的合成与评价

  摘要：

  作为我们正在进行的旨在抑制几丁质合酶的计划的一部分，我们已经制备了一种新的C-糖基核苷作为UDP-GlcNAc的代谢稳定底物类似物。合成策略依赖于核苷和氨基C-糖基部分与L-酒石酸的连续偶联。但是，该化合物仅抑制弱几丁质合酶I，IC（50）值为20 mM。

  DOI：

  10.1016/s0008-6215(01)00191-4
• 作为产物：
  描述：

  dimethyl 2,3-O-benzylidene-L-tartrate 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 以54%的产率得到(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid monomethyl ester
  参考文献：
  名称：

  几丁质合酶抑制剂C-糖基核苷的合成与评价

  摘要：

  作为我们正在进行的旨在抑制几丁质合酶的计划的一部分，我们已经制备了一种新的C-糖基核苷作为UDP-GlcNAc的代谢稳定底物类似物。合成策略依赖于核苷和氨基C-糖基部分与L-酒石酸的连续偶联。但是，该化合物仅抑制弱几丁质合酶I，IC（50）值为20 mM。

  DOI：

  10.1016/s0008-6215(01)00191-4

文献信息

• Depsipeptide Dendrimers
  作者：Jürgen Kress、Alexander Rosner、Andreas Hirsch

  DOI：10.1002/(sici)1521-3765(20000117)6:2<247::aid-chem247>3.0.co;2-m

  日期：2000.1.17

  The convergent synthesis of a new class of chiral dendrimers is described. Owing to their structural resemblance to depsipeptides they are called depsipeptide dendrimers. The ex-chiral pool synthesis starts from (R,R)-, (S,S)-, and meso-tartaric acid as branching units and dipeptides or tripeptides consisting of glycine, (L)-alanine, and (L)-leucine as chiral-spacer building blocks. The key intermediates

  描述了新型手性树状聚体的收敛合成。由于它们与大肽肽的结构相似，它们被称为大肽肽树状聚合物。前手性池的合成起始于（R，R）-，（S，S）-和内消旋酒石酸作为分支单元以及由甘氨酸，（L）-丙氨酸和（L）-亮氨酸组成的二肽或三肽作为手性垫片的组成部分。这种二肽树状大分子聚合组装的关键中间体是肽-酒石酸共轭物13a，b，19a，b，25和27，其中包含一个未保护的肽链C末端（13a，b，25）或酒石酸末端的两个未保护的羟基。通过使用立体异构结构单元的不同组合，合成了第三代的丹德拉，并对其进行了完全表征。
• Solid-state and solution conformational analysis of tartrate-derived 1,3-dioxolanes and 1,3,2-dioxaborolanes
  作者：William R. Roush、Andrew M. Ratz、Jill A. Jablonowski

  DOI：10.1021/jo00033a027

  日期：1992.3

  Solid-state (X-ray) and solution conformational analyses of tartrate ester derived 1,3-dioxolanes and 1,3,2-dioxaborolanes are described. The solid-state conformation of dimethyl benzylidenetartrate (5) was found to be one in which the two carbomethoxy groups are pseudoaxial and the ester carbonyls eclipse the adjacent dioxolane C-O bonds. This parallels exactly the conformation previously proposed for the 1,3,2-dioxaborolane unit in the transition state of the reactions of tartrate ester modified allylboronates 1-3 and aldehydes. A correlation was developed between the solution and solid-state conformations of 1,3-dioxolanes 5-7 based on the observed J4,5 coupling constants and the H-4-C-C-H-5 dihedral angle obtained from the X-ray crystal structures. A high resolution variable-temperature H-1 NMR study of 1,3-dioxolane 5 in THF-d8 revealed that J4,5 decreased from 3.72 Hz at 23-degrees-C to 2.91 Hz at -80-degrees-C, providing evidence that the diaxial conformation is increasingly favored as the temperature is decreased. A high resolution variable-temperature H-1 NMR study of ortho ester 12, prepared from dimethyl tartrate and trimethyl orthoacetate, in THF-d8 similarly revealed J4,5 = 5.25 Hz at 23-degrees-C and J4,5 = 4.60 Hz at -80-degrees-C. An analogous solution conformation analysis was also performed with 1,3,2-dioxaborolane derivatives 16 and 17 prepared from methyl trifluoroethyl tartrate (15). Variable-temperature H-1 NMR analysis of 17 in toluene-d8 revealed that J4,5 decreased to a value of J4,5 = 5.0 Hz at 23-degrees-C to J4,5 = 4.3 Hz at -60-degrees-C. The significance of these data to the mechanism of asymmetric induction in the reactions of the tartrate ester modified allylboronates 1-3 and aldehydes is discussed.
• Synthesis and evaluation of a C-glycosyl nucleoside as an inhibitor of chitin synthase
  作者：Juan Xie、Annie Thellend、Hubert Becker、Anne Vidal-Cros

  DOI：10.1016/s0008-6215(01)00191-4

  日期：2001.8

  As part of our ongoing program devoted to inhibit chitin synthases, we have prepared a novel C-glycosyl nucleoside as metabolically stable substrate analog of UDP-GlcNAc. The synthetic strategy relies on the consecutive coupling of nucleoside and amino C-glycosyl moieties with L-tartaric acid. However, this compound inhibited only weakly chitin synthase I, with an IC(50) value of 20 mM.

  作为我们正在进行的旨在抑制几丁质合酶的计划的一部分，我们已经制备了一种新的C-糖基核苷作为UDP-GlcNAc的代谢稳定底物类似物。合成策略依赖于核苷和氨基C-糖基部分与L-酒石酸的连续偶联。但是，该化合物仅抑制弱几丁质合酶I，IC（50）值为20 mM。