2-((2S,4S)-4-allyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl)acetic acid | 92572-50-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-((2S,4S)-4-allyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl)acetic acid
• 英文别名: 2-[(2S,4S)-2-tert-butyl-5-oxo-4-prop-2-enyl-1,3-dioxolan-4-yl]acetic acid
• CAS: 92572-50-4
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: SPRAZNHBMCWGJB-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-((2S,4S)-4-allyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl)acetic acid 在 N-羟基-7-氮杂苯并三氮唑 、 sodium hydride 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 1.17h， 生成 benzyl 1-(2-((S)-3-((benzyloxy)carbonyl)-3-hydroxyhex-5-enamido)ethyl)-2-hydroxy-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  Chemical Synthesis of Staphyloferrin B Affords Insight into the Molecular Structure, Iron Chelation, and Biological Activity of a Polycarboxylate Siderophore Deployed by the Human Pathogen Staphylococcus aureus

  摘要：

  Staphyloferrin B (SB) is a citrate-based polycarboxylate siderophore produced and utilized by the human pathogen Staphylococcus aureus for acquiring iron when colonizing the vertebrate host. The first chemical synthesis of SB is reported, which enables further molecular and biological characterization and provides access to structural analogues of the siderophore. Under conditions of iron limitation, addition of synthetic SB to bacterial growth medium recovered the growth of the antibiotic resistant community isolate S. aureus USA300 JE2. Two structural analogues of SB, epiSB and SBimide, were also synthesized and employed to investigate how epimerization of the citric acid moiety or imide formation influence its function as a siderophore. Epimerization of the citric acid stereocenter perturbed the iron-binding properties and siderophore function of SB as evidenced by experimental and computational modeling studies. Although epiSB provided growth recovery to S. aureus USA300 JE2 cultured in iron-deficient medium, the effect was attenuated relative to that of SB. Moreover, SB more effectively sequestered the Fe(Ill) bound to human holo-transferrin, an iron source of S. aureus, than epiSB. SBimide is an imide analogous to the imide forms of other citric acid siderophores that are often observed when these molecules are isolated from natural sources. Here, SBimide is shown to be unstable, converting to native SB at physiological pH. SB is considered to be a virulence factor of S. aureus, a pathogen that poses a particular threat to public health because of the number of drug-resistant strains emerging in hospital and community settings. Iron acquisition by S. aureus is important for its ability to colonize the human host and cause disease, and new chemical insights into the structure and function of SB will inform the search for new therapeutic strategies for combating S. aureus infections.

  DOI：

  10.1021/jacs.5b04557
• 作为产物：
  描述：

  特戊醛 在 硫酸 、 对甲苯磺酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 57.0h， 生成 2-((2S,4S)-4-allyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl)acetic acid
  参考文献：
  名称：

  （R，R）-根铁铁蛋白，（S，S）-根铁铁蛋白和（R，S，R）-葡萄铁蛋白A的流线型合成

  摘要：

  （R，R）-根铁蛋白和（R，S，R）-葡萄铁蛋白A是羧酸盐型铁载体。从（R）-柠檬酸开始已经完成了它们的流线型合成。这些合成的关键步骤是化学酶酯水解。（S，S）-根铁蛋白可通过从（S）-柠檬酸盐衍生的合成子开始的多步合成来获得。

  DOI：

  10.1016/j.phytol.2019.07.012

文献信息

• (α-Alkylation of α-heterosubstituted carboxylic acids without racemization
  作者：Dieter Seebach、Reto Naef、Giorgio Calderari

  DOI：10.1016/s0040-4020(01)82417-0

  日期：1984.1

  α-Hydroxy- and α-mercapto-carboxylic acids are condensed with pivalaldehyde to give 2-t-butyl-5-substituted-l,3-dioxolanones or 1,3-oxathiolanones (2); the predominate CK-isomers are separated by crystallization. The cis-disubstituted heterocycles 2 derived from lactic, mandelic and malic acid furnish, after deprotonation with LDA, reaction with electrophiles such as alkyl halides, aldehydes and ketones

  将α-羟基和α-巯基羧酸与新戊醛缩合，生成2-叔丁基-5-取代的-1,3-二氧戊环酮或1,3-氧杂硫杂环戊酮（2）；主要的CK异构体通过结晶分离。的顺式二取代的杂环2从乳酸，扁桃酸和苹果酸配料衍生，用LDA，与亲电子试剂如烷基卤化物，醛和酮，去质子化反应后，水解α-α支链羟基-羧酸（3，6，8，9，10）。这些归因于质子在α-CO位置上的整体置换而保留了构型。旋光羧酸是α-烷基化的，没有消旋作用，也没有使用手性助剂（“手性的自我复制”方案I）。非对映选择性（ds）通常> 95％（表1、2和20-25）。
• A concise synthesis of (R)- and (S)-α-alkyl isoserines from d- and l-malic acids
  作者：Yan Huang、Yong-Bo Zhang、Zhi-Ce Chen、Peng-Fei Xu

  DOI：10.1016/j.tetasy.2006.11.033

  日期：2006.11

  A simple and diastereoselective method for the synthesis of (R)- and (S)-α-alkyl isoserines has been developed in four steps starting from commercially available d- and l-malic acid, respectively. This approach features stereocontrolled alkylation of 2-(2-tert-butyl-5-oxo-1,3-dioxolan-4-yl)acetic acid and proceeds through a methylcarbamate via a Curtius rearrangement.

  已经分别从市售的d-和1-苹果酸开始以四个步骤开发了一种简单的非对映选择性的合成（R）-和（S）-α-烷基异丝氨酸的方法。该方法的特征在于2-（2-叔丁基-5-氧代-1，3-二氧戊环-4-基）乙酸的立体控制烷基化，并通过Curtius重排通过氨基甲酸甲酯进行。
• Identification of a New Sex Pheromone from the Silk Dragline of the Tropical Wandering SpiderCupiennius salei
  作者：Mirjam Papke、Stefan Schulz、Harald Tichy、Ewald Gingl、Rudolf Ehn

  DOI：10.1002/1521-3773(20001201)39:23<4339::aid-anie4339>3.0.co;2-t

  日期：2000.12.1
• SEEBACH, D.;NAEF, R.;CALDERARI, G., TETRAHEDRON, 1984, 40, N 8, 1313-1324
  作者：SEEBACH, D.、NAEF, R.、CALDERARI, G.

  DOI：——

  日期：——