di-tert-butyl (S)-3-tert-butoxycarbonyl-(R)-2-hydroxypentanedioate | 943859-06-1

• 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)-3-tert-butoxycarbonyl-(R)-2-hydroxypentanedioate
• 英文别名: tritert-butyl (1R,2S)-1-hydroxypropane-1,2,3-tricarboxylate
• CAS: 943859-06-1
• 化学式: C₁₈H₃₂O₇
• 分子量: 360.448
• InChiKey: QJCABHGKUYBYSD-WCQYABFASA-N

物化性质

• 沸点：
  426.3±45.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (S)-3-tert-butoxycarbonyl-(R)-2-hydroxypentanedioate 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 53.0h， 生成 (E)-caffeoylisocitric acid-d₁
  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：

  di-tert-butyl-(S)-2-allyl-(R)-3-hydroxysuccinate 在 4-二甲氨基吡啶 、 sodium periodate 、 ruthenium(III) chloride trihydrate 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 64.0h， 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

文献信息

• Total Synthesis and Stereochemical Reassignment of Citrafungin A
  作者：Zongjia Chen、Angus Robertson、Jonathan M. White、Mark A. Rizzacasa

  DOI：10.1021/acs.orglett.9b03830

  日期：2019.12.6

  The stereoselective 12-step total synthesis of the reassigned structure for citrafungin A (1a) via cyclobutene diester 10 is described. Key steps involved a formal [2 + 2]-cycloaddition, oxa-Michael/cyclobutanone ring-opening cascade to secure the alkyl citrate core, and asymmetric vinylzinc addition to form the C6 stereocenter. In addition, no oxidative adjustments are required to secure the citrate

  描述了通过环丁烯二酯10进行的柠檬黄素A（1a）重新分配结构的立体选择性12步全合成。关键步骤涉及正式的[2 + 2]-环加成反应，氧杂-Michael /环丁酮开环级联反应以固定柠檬酸烷基酯核心，以及不对称的乙烯基锌加成反应以形成C6立体中心。另外，不需要氧化调节来确保柠檬酸盐的氧化水平。
• 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。
• Comparison of Non-ephedrine Constituents from <i>Ephedra</i> Plants Cultivated in Japan
  作者：Kengo Hayashi、Yuki Miyao、Hina Matsui、Takao Yamaura、Ken Tanaka、Mariko Baba、Hiroaki Hayashi

  DOI：10.1248/cpb.c24-00043

  日期：2024.4.17

  Ephedra plants, the main components of which are ephedrine alkaloids, are used as traditional medicines in Eastern Asian countries. In this study, we isolated non-ephedrine constituents from various Ephedra plant species cultivated in Japan. HPLC analysis suggested that kynurenic acid and its derivatives accumulated in a wide range of Ephedra plant species. Furthermore, a large amount of (2R,3S)-O-benzoyl

  麻黄植物的主要成分是麻黄碱，在东亚国家被用作传统药物。在这项研究中，我们从日本种植的各种麻黄植物中分离出了非麻黄碱成分。 HPLC 分析表明犬尿酸及其衍生物在多种麻黄植物中积累。此外，还从E. intermedia中分离出大量的( 2R , 3S ) -O-苯甲酰基异柠檬酸酯。这项研究表明麻黄植物具有多种非麻黄碱成分。  全尺寸图像
• 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.