di-tert-butyl-(S)-2-allyl-(R)-3-hydroxysuccinate | 943859-04-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: di-tert-butyl-(S)-2-allyl-(R)-3-hydroxysuccinate
• 英文别名: ditert-butyl (2R,3S)-2-hydroxy-3-prop-2-enylbutanedioate
• CAS: 943859-04-9
• 化学式: C₁₅H₂₆O₅
• 分子量: 286.368
• InChiKey: SQGRZRXZOSEABQ-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  di-tert-butyl-(S)-2-allyl-(R)-3-hydroxysuccinate 在 4-二甲氨基吡啶 、 sodium periodate 、 ruthenium(III) chloride trihydrate 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 15.0h， 生成 (3S,4R)-4-acetyloxy-5-[(2-methylpropan-2-yl)oxy]-3-[(2-methylpropan-2-yl)oxycarbonyl]-5-oxopentanoic acid
  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 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 di-tert-butyl-(S)-2-allyl-(R)-3-hydroxysuccinate
  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

• Formal Total Synthesis of (+)-Citrafungin A
  作者：Sammi Tsegay、Helmut Hügel、Mark A. Rizzacasa

  DOI：10.1071/ch09182

  日期：——

  inhibitor (+)-citrafungin A 1 is described. The key steps include a selective vinyl anion addition of the anion derived from iodide 10 to the lactone 9 and lactonization/selective deprotection of the allylic alcohols 8 and 23 to afford the citrafungin lactone. Esterification with the isocitrate 6 afforded citrafungin A tetra-t-butyl ester 5 which completed the formal total synthesis.

  描述了真菌GGTase I抑制剂（+）-西拉芬净A 1的正式全合成。关键步骤包括将来自碘化物10的阴离子选择性乙烯基阴离子加到内酯9中，以及将烯丙醇8和23进行内酯化/选择性脱保护，以得到西他芬净内酯。酯化与异柠檬酸6得到citrafungin甲四吨丁基酯5即完成了正式的全合成。
• 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.