benzyl (2R,3R)-3-hydroxy-2-<(2,6-dimethoxybenzoyl)-oxy>butanedioate | 158732-36-6

• 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: benzyl (2R,3R)-3-hydroxy-2-<(2,6-dimethoxybenzoyl)-oxy>butanedioate
• 英文别名: dibenzyl (2R,3R)-2-(2,6-dimethoxybenzoyl)oxy-3-hydroxybutanedioate
• CAS: 158732-36-6
• 化学式: C₂₇H₂₆O₉
• 分子量: 494.498
• InChiKey: RBBYTKBORHIJFF-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl (2R,3R)-3-hydroxy-2-<(2,6-dimethoxybenzoyl)-oxy>butanedioate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.67h， 以100%的产率得到-2-<(2,6-dimethoxybenzoyl)oxy>-3-hydroxybutanedioic acid
  参考文献：
  名称：

  Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines: Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst.

  摘要：

  通过手性酒石酸衍生的酰基硼烷介导的源自 6-甲基的硅烯醇醚的醇醛缩合，完成了在 6 位具有 2-羟基化烷基的 1, 3-二恶英-4-酮的新型对映选择性合成-1, 3-二恶英-4-酮与非手性醛的衍生物。

  DOI：

  10.1248/cpb.42.839
• 作为产物：
  描述：

  2,6-二甲氧基苯甲酸 、 dibenzyl (2R,3R)-2,3-dihydroxybutanedioate 以 二氯甲烷 为溶剂， 反应 48.0h， 以86%的产率得到benzyl (2R,3R)-3-hydroxy-2-<(2,6-dimethoxybenzoyl)-oxy>butanedioate
  参考文献：
  名称：

  Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines: Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst.

  摘要：

  通过手性酒石酸衍生的酰基硼烷介导的源自 6-甲基的硅烯醇醚的醇醛缩合，完成了在 6 位具有 2-羟基化烷基的 1, 3-二恶英-4-酮的新型对映选择性合成-1, 3-二恶英-4-酮与非手性醛的衍生物。

  DOI：

  10.1248/cpb.42.839

文献信息

• Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines: Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst.
  作者：Masayuki SATO、Satoshi SUNAMI、Yoshiaki SUGITA、Chikara KANEKO

  DOI：10.1248/cpb.42.839

  日期：——

  A novel enantioselective synthesis of 1, 3-dioxin-4-ones having a 2-hydroxylated alkyl group at the 6-position has been accomplished by chiral tartaric acid-derived acylborane-mediated aldol condensation of the silyl enol ether derived from 6-methyl-derivatives of 1, 3-dioxin-4-one with achiral aldehydes.

  通过手性酒石酸衍生的酰基硼烷介导的源自 6-甲基的硅烯醇醚的醇醛缩合，完成了在 6 位具有 2-羟基化烷基的 1, 3-二恶英-4-酮的新型对映选择性合成-1, 3-二恶英-4-酮与非手性醛的衍生物。
• Sato Masayuki, Sunami Satoshi, Sugita Yoshiaki, Kaneko Chikara, Chem. and Pharm. Bull, 42 (1994) N 4, S 839-845
  作者：Sato Masayuki, Sunami Satoshi, Sugita Yoshiaki, Kaneko Chikara

  DOI：——

  日期：——
• Enantioselective Synthesis of Cyclothiazide Analogues:  Novel Probes of the Stereospecific Actions of Benzothiadiazines at AMPA-Type Glutamate Receptors
  作者：Yuefei Hu、Kelvin A. Yamada、David K. Chalmers、Durga P. Annavajjula、Douglas F. Covey

  DOI：10.1021/ja9525317

  日期：1996.1.1

  The stereospecific interactions of the eight stereoisomers of dihydromethylcyclothiazide, an analogue of cyclothiazide, with AMPA-type glutamate receptors was investigated using electrophysiological methods that measured the ability of each stereoisomer to inhibit AMPA receptor desensitization. The eight stereoisomers were obtained by HPLC separation of four pairs of enantiomerically pure (>95% ee) diastereomers prepared from (1R-exo)-, (1R-endo)-, (1S-exo)-, and (1S-endo)-2-methylbicyclo[2.2.1]heptane-2-carboxaldehyde intermediates. The desensitization process was blocked most potently by [1S-[1 alpha,2 alpha(R*),4 alpha]]-dihydromethylcyclothiazide, one of the stereoisomers prepared from the (1S-endo)-carboxaldehyde. The smallest effects on the desensitization process were found for the four stereoisomers prepared from the (1R-exo)- and (1R-endo)-carboxaldehydes. Significant differences in the ability to inhibit desensitization were observed between all diastereomer pairs except those prepared from the (1S-exo)-carboxaldehyde.