(4R,6R)-4-<oxy>-6,7-epoxyheptene | 130459-43-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4R,6R)-4-<oxy>-6,7-epoxyheptene
• 英文别名: tert-butyl-dimethyl-[(2R)-1-[(2R)-oxiran-2-yl]pent-4-en-2-yl]oxysilane
• CAS: 130459-43-7
• 化学式: C₁₃H₂₆O₂Si
• 分子量: 242.434
• InChiKey: ODPNBZUXELPFKT-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,6R)-4-<oxy>-6,7-epoxyheptene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到1-(oxiran-2-yl)pent-4-en-2-ol
  参考文献：
  名称：

  Resolution of 2-Silyloxy-1-oxiranyl-4-pentenes by HKR: Total Synthesis of (5S,7R)-Kurzilactone

  摘要：

  利用雅各布森水解动力学解析法（HKR）制备了对映体纯度较高的同系和反系-2-硅氧基-1-环氧乙烷-4-戊烯。在关键步骤中采用环氧化物开环反应和 RCM 反应的途径，在 (5S,7R)-kurzilactone 的全合成中使用了以这种方法生成的已解析环氧戊烯醇。

  DOI：

  10.1055/s-2005-922774
• 作为产物：
  描述：

  (2S,4R)-2-(N-Benzyl-N-methylamino)-4-<oxy>-6-hepten-1-ol 在 sodium hydroxide 、 四丁基氯化铵 作用下， 以 氯仿 为溶剂， 反应 0.75h， 生成 (4R,6R)-4-<oxy>-6,7-epoxyheptene
  参考文献：
  名称：

  Synthetic Studies on the Polyene Macrolide Antibiotics. Development of syn- and anti-1,3-Diol Subunits and Assembly of the Polyacetate Region of Amphotericin B

  摘要：

  The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric beta-amino aldehyde (7) and the stereospecific transformation of a vicinal amino alcohol to an epoxide. The resultant diasteromeric silyl-protected epoxy alcohols (10s and 10a) serve as convenient precursors to the isomeric diol aldehyde derivatives 13, 13-ent, and 16. One of these fragments, compound 13, has been exploited in a highly convergent synthesis of the C1-C13 polyacetate segment of amphotericin B.

  DOI：

  10.1021/jo00129a019

文献信息

• Studies toward the application of oxazolineepoxide equivalency in 1,3-asymmetric induction
  作者：Kenneth R. Overly、J.Michael Willams、Glenn J. McGarvey

  DOI：10.1016/s0040-4039(00)97679-2

  日期：1990.1
• Efficient Asymmetric Total Syntheses of Cryptocarya Triacetate, Cryptocaryolone, and Cryptocaryolone Diacetate
  作者：Xiaolei Wang、Wenkuan Wang、Huaiji Zheng、Yingpeng Su、Tuo Jiang、Yongping He、Xuegong She

  DOI：10.1021/ol901024t

  日期：2009.7.16

  Concise and efficient asymmetric total syntheses of three substituted alpha-pyrone-type natural products have been accomplished via 7-9 steps from 5b in high overall yields, which involve linchpin coupling, ring-closing metathesis, and a tandem sequence of deacetylation and intramolecular oxa-Michael addition as the key steps.
• OVERLY, KENNETH R.;WILLIAMS, J. MICHAEL;MCGARVEY, GLENN J., TETRAHEDRON LETT., 31,(1990) N2, C. 4573-4576
  作者：OVERLY, KENNETH R.、WILLIAMS, J. MICHAEL、MCGARVEY, GLENN J.

  DOI：——

  日期：——
• Synthetic Studies on the Polyene Macrolide Antibiotics. Development of syn- and anti-1,3-Diol Subunits and Assembly of the Polyacetate Region of Amphotericin B
  作者：Glenn J. McGarvey、Jeffrey A. Mathys、Kenneth J. Wilson、Kenneth R. Overly、Paul T. Buonora、P. Grant Spoors

  DOI：10.1021/jo00129a019

  日期：1995.12

  The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric beta-amino aldehyde (7) and the stereospecific transformation of a vicinal amino alcohol to an epoxide. The resultant diasteromeric silyl-protected epoxy alcohols (10s and 10a) serve as convenient precursors to the isomeric diol aldehyde derivatives 13, 13-ent, and 16. One of these fragments, compound 13, has been exploited in a highly convergent synthesis of the C1-C13 polyacetate segment of amphotericin B.
• Resolution of 2-Silyloxy-1-oxiranyl-4-pentenes by HKR: Total Synthesis of (5<i>S</i>,7<i>R</i>)-Kurzilactone
  作者：Jinsung Tae、Young-Ju Kim

  DOI：10.1055/s-2005-922774

  日期：——

  Enantiomerically pure syn- and anti-2-silyloxy-1-oxiranyl-4-pentenes were prepared by using Jacobsen’s hydrolytic kinetic resolution (HKR) method. A resolved epoxypentenol generated in this fashion was used in the total synthesis of (5S,7R)-kurzilactone by a pathway employing epoxide ring-opening and RCM reactions in key steps.

  利用雅各布森水解动力学解析法（HKR）制备了对映体纯度较高的同系和反系-2-硅氧基-1-环氧乙烷-4-戊烯。在关键步骤中采用环氧化物开环反应和 RCM 反应的途径，在 (5S,7R)-kurzilactone 的全合成中使用了以这种方法生成的已解析环氧戊烯醇。