di-tert-butyl (R)-2-acetoxy-(S)-3-allylsuccinate | 1073132-30-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: di-tert-butyl (R)-2-acetoxy-(S)-3-allylsuccinate
• 英文别名: ditert-butyl (2R,3S)-2-acetyloxy-3-prop-2-enylbutanedioate
• CAS: 1073132-30-5
• 化学式: C₁₇H₂₈O₆
• 分子量: 328.406
• InChiKey: KYHYPJCWNHWEGD-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (R)-2-acetoxy-(S)-3-allylsuccinate 在 sodium periodate 、 ruthenium(III) chloride trihydrate 、 potassium carbonate 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 59.0h， 生成 di-tert-butyl (S)-3-tert-butoxycarbonyl-(R)-2-hydroxypentanedioate
  参考文献：
  名称：

  Isolation, total synthesis and quantification of caffeoylisocitric acid, a characteristic ingredient of the superfood amaranth

  摘要：

  Amaranth is regarded as a new "super-vegetable" in western countries, albeit it is consumed for centuries in Africa and Asia. In addition to common carotenoids, flavonoids and polyphenols, caffeoylisocitric acid has been described as amaranth type-specific secondary metabolite. Remarkably, nothing is known on biological effects of this specific polyphenol. Here we detail a concise, diastereoselective synthesis of caffeoylisocitric acid, deuterium-labelling studies and a quantitative determination of the caffeoylisocitric acid content of three different amaranth types. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2019.06.033
• 作为产物：
  描述：

  2-叔丁基-1,3-二异丙基异脲 在 4-二甲氨基吡啶 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 di-tert-butyl (R)-2-acetoxy-(S)-3-allylsuccinate
  参考文献：
  名称：

  Isolation, total synthesis and quantification of caffeoylisocitric acid, a characteristic ingredient of the superfood amaranth

  摘要：

  Amaranth is regarded as a new "super-vegetable" in western countries, albeit it is consumed for centuries in Africa and Asia. In addition to common carotenoids, flavonoids and polyphenols, caffeoylisocitric acid has been described as amaranth type-specific secondary metabolite. Remarkably, nothing is known on biological effects of this specific polyphenol. Here we detail a concise, diastereoselective synthesis of caffeoylisocitric acid, deuterium-labelling studies and a quantitative determination of the caffeoylisocitric acid content of three different amaranth types. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2019.06.033

文献信息

• Total Synthesis of Citrafungin A
  作者：Frederick Calo、Jeffery Richardson、Anthony G. M. Barrett

  DOI：10.1021/jo801708q

  日期：2008.12.19

  The antifungal natural product citrafungin A was synthesized using, as key steps, an asymmetric aldol reaction of a chiral oxazolidinone, diastereoselective alkylation of a chiral 1,3-dioxolan-2-one, semihydrogenation of an enyne, and selective methyl ester deprotection.
• Isolation, total synthesis and quantification of caffeoylisocitric acid, a characteristic ingredient of the superfood amaranth
  作者：Tianyi Zhou、Benedikt Ringbeck、Nils Helge Schebb、Jürgen Scherkenbeck

  DOI：10.1016/j.tet.2019.06.033

  日期：2019.8

  Amaranth is regarded as a new "super-vegetable" in western countries, albeit it is consumed for centuries in Africa and Asia. In addition to common carotenoids, flavonoids and polyphenols, caffeoylisocitric acid has been described as amaranth type-specific secondary metabolite. Remarkably, nothing is known on biological effects of this specific polyphenol. Here we detail a concise, diastereoselective synthesis of caffeoylisocitric acid, deuterium-labelling studies and a quantitative determination of the caffeoylisocitric acid content of three different amaranth types. (C) 2019 Elsevier Ltd. All rights reserved.