(S)-4-benzyl-3-((R)-2-ethylpent-4-enoyl)oxazolidin-2-one | 130710-56-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-4-benzyl-3-((R)-2-ethylpent-4-enoyl)oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(2R)-2-ethylpent-4-enoyl]-1,3-oxazolidin-2-one
• CAS: 130710-56-4
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: AFRXRIBNDKMFRN-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-((R)-2-ethylpent-4-enoyl)oxazolidin-2-one 在 sodium periodate 、 四氧化锇 、 锂硼氢 、 正丁基锂 、 N-甲基吲哚酮 、 三丁基膦 作用下， 生成 tert-Butyl-[(E)-(R)-2-ethyl-5-((S)-2-ethyl-1,4-dioxa-spiro[4.5]dec-2-yl)-pent-4-enyloxy]-diphenyl-silane
  参考文献：
  名称：

  The first total synthesis and absolute stereochemistry of plakortone G from the Jamaican sponge Plakortis sp.

  摘要：

  Total synthesis of plakortone G (1), a secondary metabolite of the Jamaican sponge Plakortis sp., was successfully achieved. The absolute configuration of this molecule was determined by comparison of the synthetic diastereomers with reported data to possess the (4R,8R)-configuration 14. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.169
• 作为产物：
  描述：

  (S)-4-苄基-2-唑烷酮 在 正丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 生成 (S)-4-benzyl-3-((R)-2-ethylpent-4-enoyl)oxazolidin-2-one
  参考文献：
  名称：

  热蛋白质组图谱可有效鉴定核糖体不稳定的恶唑烷酮

  摘要：

  鉴定具有生物活性的小分子的靶标是一项具有挑战性的工作，目前尚无通用的解决方案。经典的亲和纯化实验需要功能化生物活性化合物并将其连接到固体支持物上，这可能会干扰靶标结合。基于现代质谱的蛋白质组学技术已部分规避了此问题，是热蛋白质组分析（TPP），它同时确定了未修饰的小分子对整个蛋白质组的热稳定性的影响。在这里，我们使用TPP来识别基于经常用作手性助剂的恶唑烷酮的新发现的自噬抑制剂的作用方式。出乎意料的是，发现所有核糖体蛋白中有很大一部分被抑制剂破坏了稳定性，

  DOI：

  10.1016/j.tet.2021.132118

文献信息

• Efficient Approach to Fluvirucins B₂−B₅, Sch 38518, and Sch 39185. First Synthesis of their Aglycon, via CM and RCM Reactions
  作者：Enric Llàcer、Fèlix Urpí、Jaume Vilarrasa

  DOI：10.1021/ol901030f

  日期：2009.8.6

  fluvirucins B2−B5, Sch 38518, and Sch 39185) is reported for the first time. A ring-closing metathesis (RCM) generated the C6−C7 double bond, which by catalytic hydrogenation (in toluene) gave the desired epimer with a 9:1 diastereoselection. Azide 8a and carboxylic acid 5 came from ethyl-branched fragments C9−C13 (CHO at C9) and C1−C5 via an asymmetric allylation of the former and a cross metathesis

  首次报道了通向氟维他星B 2-5（氟维他星B 2 -B 5，Sch 38518和Sch 39185的常见糖苷配基）的途径。闭环复分解（RCM）生成了C6-C7双键，该双键通过催化氢化（在甲苯中）以9：1的非对映体选择得到所需的差向异构体。叠氮化物8a和羧酸5来自乙基支化的片段C9-C13（CHO在C9）和C1-C5，它们通过前者的不对称烯丙基化和交叉易位（CM）然后是酮甲基化（含20 mol％的DMF）作为牺牲性添加剂）。
• Total Synthesis of Peloruside A through Kinetic Lactonization and Relay Ring-Closing Metathesis Cyclization Reactions
  作者：Thomas R. Hoye、Junha Jeon、Lucas C. Kopel、Troy D. Ryba、Manomi A. Tennakoon、Yini Wang

  DOI：10.1002/anie.201002293

  日期：2010.8.16

  The other side: A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5–C9 valerolactone from the C2‐symmetric ketone 3, and a relay ring‐closing metathesis reaction to produce a dehydrovalerolactone 2. A new isomer of 1, the valerolactone isopeloruside A (iso‐1), was identified. MOM=methoxymethyl.

  另一方面：描述了peloruside A( 1 )的收敛全合成。关键的策略特征是非对映选择性内酯化从C 2对称酮3生成 C5-C9 戊内酯，以及中继闭环复分解反应生成脱氢戊内酯2。鉴定了1的新异构体，即异戊内酯异戊内酯 A ( iso-1 )。MOM=甲氧基甲基。
• Synthesis of (+)-Tacamonine via Stereoselective Radical Cyclization
  作者：Myles W. Smith、Jasmin Ferreira、Roger Hunter、Gerhard A. Venter、Hong Su

  DOI：10.1021/acs.orglett.9b03308

  日期：2019.11.1

  A concise, asymmetric synthesis of the indole alkaloid (+)-tacamonine is reported involving a stereoselective radical cyclization of a 1-phenylsulfanyl tetrahydro-β-carboline bearing a pendant enoate ester side chain as a key step. In this process, a single stereocenter in the side chain allows for the formation of two stereocenters of the natural product in a highly diastereoselective fashion. Computational

  据报道，吲哚生物碱（+）-塔卡莫宁的简明，不对称合成涉及关键步骤，该方法涉及带有侧链烯醇酸酯侧链的1-苯基硫烷基四氢-β-咔啉的立体选择性自由基环化。在此过程中，侧链中的单个立体中心可以以高度非对映选择性的方式形成天然产物的两个立体中心。对这一关键环化反应的计算研究支持了实验观察到的结果，并阐明了影响其立体选择性的因素。
• Assignment of stereochemistry in the oligomycin/rutamycin/cytovaricin family of antibiotics. Asymmetric synthesis of the rutamycin spiroketal synthon
  作者：David A. Evans、Dale L. Rieger、Todd K. Jones、Stephen W. Kaldor

  DOI：10.1021/jo00313a011

  日期：1990.12

  The absolute stereochemistry of the rutamycin antibiotics 2a,b has been established through asymmetric synthesis of the known degradation product 4. One of the key steps in the assemblage process involves acylation of the metalated hydrazone 6 with the N-methoxy-N-methyl amide 5. Both of these enantiomerically pure intermediates have been prepared in good overall yield and high diastereoselectivity (de > 94%). All absolute stereochemical relationships were established through alkylation and aldol bond constructions using N-acyloxazolidinone chiral auxiliaries. Subjection of 17 to acid hydrolysis/deprotection resulted in loss of protecting groups and subsequent spiroketalization to 19 (80%). Silylation of the secondary alcohol in 19 was followed by a samarium-catalyzed Meerwein-Ponndorf-Verley reduction to provide the equatorial alcohol 20 in excellent yield and stereoselectivity (de = 97%). Control experiments indicate that this surprisingly stereoselective reaction operates under kinetic control and that the observed stereochemical outcome may be the result of coordination of the reactive reducing agent to the axial spiroketal oxygen. Conversion of 20 to triol 4 afforded material that is identical with the rutamycin degradation product in all respects. These results establish that the absolute stereochemistry of the rutamycins is as shown (2a,b).
• EVANS, DAVID A.;RIEGER, DALE L.;JONES, TODD K.;KALDOR, STEPHEN W., J. ORG. CHEM., 55,(1990) N6, C. 6260-6268
  作者：EVANS, DAVID A.、RIEGER, DALE L.、JONES, TODD K.、KALDOR, STEPHEN W.

  DOI：——

  日期：——