2-((2S,5S)-5-methyl-5-((R)-oxiran-2-yl)tetrahydrofuran-2-yl)propan-2-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-((2S,5S)-5-methyl-5-((R)-oxiran-2-yl)tetrahydrofuran-2-yl)propan-2-ol
• 英文别名: 2-[(2S,5S)-5-methyl-5-[(2R)-oxiran-2-yl]oxolan-2-yl]propan-2-ol
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: QZRANJWXTXXQQC-XKSSXDPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((2S,5S)-5-methyl-5-((R)-oxiran-2-yl)tetrahydrofuran-2-yl)propan-2-ol 在 咪唑 、 4-二甲氨基吡啶 、 copper(l) iodide 、 偶氮二甲酸二异丙酯 、 mercury(II) diacetate 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.75h， 生成 1-((benzyloxy)methyl)-4-((R,Z)-3-methyl-6-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-6-((triethylsilyl)oxy)hex-2-en-1-yl)-2-nitro-1H-pyrrole
  参考文献：
  名称：

  Total Synthesis of Heronapyrrole C

  摘要：

  A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharp less asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.

  DOI：

  10.1021/ol403246j
• 作为产物：
  描述：

  香叶醇 在 titanium(IV) isopropylate 叔丁基过氧化氢 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 (+)-Weinsaeure-diethylester 、 三乙胺 作用下， 生成 2-((2S,5S)-5-methyl-5-((R)-oxiran-2-yl)tetrahydrofuran-2-yl)propan-2-ol
  参考文献：
  名称：

  Synthesis of four stereoisomers of the higher dipteran juvenile hormone III bisepoxide

  摘要：

  The 6S,7S,10R-, 6S,7S,10S-, 6R,7R,10S- and 6R,7R,10R-stereoisomers of the juvenile hormone III bisepoxide from higher Dipteran insects have been synthesised in high stereoisomeric purity. The route involves Sharpless epoxidation of geraniol to enantiomeric epoxyalcohols, which are each elaborated via separable diastereomeric bromohydrins.

  DOI：

  10.1016/s0040-4039(00)74741-1

文献信息

• Total Synthesis of <i>ent</i>-Dioxepandehydrothyrsiferol via a Bromonium-Initiated Epoxide-Opening Cascade
  作者：Jessica Tanuwidjaja、Sze-Sze Ng、Timothy F. Jamison

  DOI：10.1021/ja9052366

  日期：2009.9.2

  In the first total synthesis of ent-dioxepandehydrothyrsiferol, the signature trans-anti-trans 7,7,6-fused tricyclic polyether framework was constructed in a single bromonium-initiated epoxide-opening cascade that incorporates both endo- and exo-selective epoxide openings, each directed by the substitution pattern of the epoxide (methyl groups). This study thus demonstrates the feasibility of a possible

  在 ent-dioxepandehydrothyrsiferol 的第一次全合成中，标志性的 trans-anti-trans 7,7,6-稠合三环聚醚框架构建在单个溴引发的环氧化物开环级联中，该级联反应结合了内选择性和外选择性环氧化物开口，每个都由环氧化物（甲基）的取代模式指导。因此，这项研究证明了可能的生物发生的可行性。
• A highly stereoselective route to substituted bis-tetrahydrofurans from 1,5-dienes.
  作者：Roger Amouroux、Gabriel Folefoc、Francine Chastrette、Maurice Chastrette

  DOI：10.1016/s0040-4039(01)92904-1

  日期：——

  Bis-tetrahydrofurans 1a and 1b, containing four chiral centers, are obtained with a 90 % isomeric purity from geranyl and neryl chlorides in four steps including two stereoselective cyclizations.

  在四个步骤（包括两个立体选择性环化）中，从香叶基氯和神经烷基氯获得具有四个手性中心的双-四氢呋喃1a和1b，其纯度为90％。
• Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades
  作者：Brian S. Underwood、Jessica Tanuwidjaja、Sze-Sze Ng、Timothy F. Jamison

  DOI：10.1016/j.tet.2013.04.041

  日期：2013.6

  Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of four stereoisomers of the higher dipteran juvenile hormone III bisepoxide
  作者：Rodney W. Rickards、Richard D. Thomas

  DOI：10.1016/s0040-4039(00)74741-1

  日期：1992.12

  The 6S,7S,10R-, 6S,7S,10S-, 6R,7R,10S- and 6R,7R,10R-stereoisomers of the juvenile hormone III bisepoxide from higher Dipteran insects have been synthesised in high stereoisomeric purity. The route involves Sharpless epoxidation of geraniol to enantiomeric epoxyalcohols, which are each elaborated via separable diastereomeric bromohydrins.
• Total Synthesis of Heronapyrrole C
  作者：Xiao-Bo Ding、Daniel P. Furkert、Robert J. Capon、Margaret A. Brimble

  DOI：10.1021/ol403246j

  日期：2014.1.17

  A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharp less asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.