(2R,3R)-1-O-tert-butoxycarbonyl-2,3-epoxy-3,7-dimethyl-octa-6-en-1-ol | 817593-95-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (2R,3R)-1-O-tert-butoxycarbonyl-2,3-epoxy-3,7-dimethyl-octa-6-en-1-ol
• 英文别名: tert-butyl [(2R,3R)-3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methyl carbonate
• CAS: 817593-95-6
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: JKDULYLQWWUFCO-IUODEOHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1-O-tert-butoxycarbonyl-2,3-epoxy-3,7-dimethyl-octa-6-en-1-ol 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 36.5h， 生成
  参考文献：
  名称：

  用于选择性激活内-区域选择性聚环氧化物羰基化的烯烃取代基。

  摘要：

  聚环氧化物底物的末端环氧化物上烯基取代基的存在提高了全内-区域-选择性串联氧杂环化成反式-顺式-反式-稠合的多环醚的产率。对于其中环氧基和链烯官能团被两个亚甲基取代基隔开的底物，还描述了一种新的溴离子诱导的内-区域选择性环化成溴氧杂环丁烷的方法。[反应：看文字]

  DOI：

  10.1021/ol048212e
• 作为产物：
  描述：

  橙花醇 在 N-甲基咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二异丙酯 作用下， 以 癸烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 (2R,3R)-1-O-tert-butoxycarbonyl-2,3-epoxy-3,7-dimethyl-octa-6-en-1-ol
  参考文献：
  名称：

  Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.04.041

文献信息

• Gold‐catalyzed <i>endo</i>‐selective Ring‐opening of Epoxides and its Application in Construction of Poly‐ethers
  作者：Kehuan Wu、Kaiwen Kang、Dan Liu、Chiyue Zhang、Xinyu Wang、Miaocheng Zhang、Qi Li

  DOI：10.1002/chem.202400234

  日期：2024.4.11

  Tetrahydropyran and tetrahydropyran‐fused poly‐ethers scaffolds are found in many classes of natural products and medicinally relevant small molecules. Here we describe a catalytic system for 6‐endo selective ring‐opening of epoxides by Au(I) or Au(III) catalyst that provides rapid access to various tetrahydropyran‐derived motifs. It also could efficiently construct the subunits of marine ladder‐like poly‐ethers through emulating the Nakanishi's hypothesis on the biosynthesis of these toxins. The synthetic utility of this method is also demonstrated in the preparation of the tricyclic core of tetrahydropyran‐containing macrolide natural products lituarines A−C.

  摘要四氢吡喃和四氢吡喃融合聚醚支架存在于许多天然产品和药用小分子中。在此，我们介绍了一种利用金（I）或金（III）催化剂进行环氧化物 6 内向选择性开环的催化系统，该系统可快速获得各种四氢吡喃衍生基团。它还可以通过模仿中西（Nakanishi）关于这些毒素生物合成的假说，有效地构建海洋梯状聚醚的亚基。在制备含四氢吡喃的大环内酯天然产物 lituarines A-C 的三环核心时，也证明了该方法的合成实用性。
• 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.
• Alkene Substituents for Selective Activation of <i>endo</i>-Regioselective Polyepoxide Oxacyclizations
  作者：Fernando Bravo、Frank E. McDonald、Wade A. Neiwert、Kenneth I. Hardcastle

  DOI：10.1021/ol048212e

  日期：2004.11.1

  The presence of an alkenyl substituent on the terminal epoxide of a polyepoxide substrate enhances the yield of all-endo-regioselective tandem oxacyclization to trans-syn-trans-fused polycyclic ethers. For a substrate in which the epoxide and alkene functional groups are separated by two methylene substituents, a novel bromonium ion-induced endo-regioselective cyclization to bromooxepane is also described

  聚环氧化物底物的末端环氧化物上烯基取代基的存在提高了全内-区域-选择性串联氧杂环化成反式-顺式-反式-稠合的多环醚的产率。对于其中环氧基和链烯官能团被两个亚甲基取代基隔开的底物，还描述了一种新的溴离子诱导的内-区域选择性环化成溴氧杂环丁烷的方法。[反应：看文字]