tert-butyldimethyl(((2R)-1-(oxiran-2-yl)propan-2-yl)oxy)silane | 866043-88-1

• 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: tert-butyldimethyl(((2R)-1-(oxiran-2-yl)propan-2-yl)oxy)silane
• 英文别名: tert-butyldimethyl(((R)-1-(oxiran-2-yl)propan-2-yl)oxy)silane；(4R)-4-tert-butyldimethylsiloxy-1,2-epoxypentane；tert-butyl-dimethyl-[(2R)-1-(oxiran-2-yl)propan-2-yl]oxysilane
• CAS: 866043-88-1
• 化学式: C₁₁H₂₄O₂Si
• 分子量: 216.396
• InChiKey: NQELNMSJKNXHHL-YHMJZVADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  tert-butyldimethyl(((2R)-1-(oxiran-2-yl)propan-2-yl)oxy)silane 在 正丁基锂 、 (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III) 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 24.75h， 生成 (2S,4R)-1-(2-allyl-1,3-dithian-2-yl)-4-((tert-butyldimethylsilyl)oxy)pentan-2-ol
  参考文献：
  名称：

  树枝状蛋白A–D及其类似物的全合成，生物学评估

  摘要：

  以市售的（R）-环氧丙烷和3-丁烯-1-醇为起始原料，经过10个步骤完成了Dendrodolides A–D（1-4）的简明全合成。合成中涉及的关键步骤是Jacobsen水解动力学拆分，2-烯丙基-1、3-二噻吩的环氧开环，山口酯化和闭环复分解（RCM）。此外，利用山口酯化在树突状多核苷酸核心的C-3位制备了一系列酯衍生物，并筛选了它们对抗癌细胞系的功效。

  DOI：

  10.1016/j.tet.2016.06.042
• 作为产物：
  描述：

  (R)-(-)-4-烯基-2-戊醇 在 咪唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 tert-butyldimethyl(((2R)-1-(oxiran-2-yl)propan-2-yl)oxy)silane
  参考文献：
  名称：

  Enantioselective synthesis of tarchonanthuslactone via iterative hydrolytic kinetic resolution

  摘要：

  A short and practical enantioselective synthesis of tarchonanthuslactone has been achieved in high diastereomeric excess using iterative Jacobsen's hydrolytic kinetic resolution and ring closing metathesis as the key steps. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.056

文献信息

• Stereoselective synthesis of ophiocerins A and C
  作者：Krishanu Show、Priti Gupta、Pradeep Kumar

  DOI：10.1016/j.tetasy.2011.06.015

  日期：2011.6

  An efficient synthesis of ophiocerins A and C has been achieved via a common intermediate. The stereogenic centers were generated by means of Jacobsen’s hydrolytic kinetic resolution and Sharpless kinetic resolution.

  经由共同的中间体已经实现了蛇绿素A和C的有效合成。借助Jacobsen的水解动力学拆分和Sharpless动力学拆分生成了立体异构中心。
• Stereoselective total synthesis of decarestrictine J
  作者：V. B. Ramanujan、Reddymasu Sreenivasulu、Murthy Chavali、Chebolu Naga Sesha Sai Pavan Kumar

  DOI：10.1007/s00706-017-1947-3

  日期：2017.10

  AbstractStereoselective total synthesis of decarestrictine J has been accomplished from inexpensive and commercially available starting materials. This concise synthesis utilizes Jacobsen’s hydrolytic kinetic resolution, regioselective ring opening of epoxide, and Yamaguchi macrolactonisation as key steps. Graphical abstract

  摘要去卡地汀J的立体选择性全合成已经由廉价且可商购的起始原料完成。这种简洁的合成方法利用了Jacobsen的水解动力学拆分，环氧化物的区域选择性开环和Yamaguchi大内酯化作为关键步骤。 图形概要
• New Silicon-Mediated, Sequential Ring Expansions of <i>n</i>-Sized 2-Cycloalkenones into Hydroxyolefinic <i>n</i> + <i>m</i> + <i>p</i> Medium-Sized Lactones:  Short Synthesis of (−)-Phoracantholide-J
  作者：Gary H. Posner、Mark A. Hatcher、William A. Maio

  DOI：10.1021/ol051854x

  日期：2005.9.1

  In only four steps from 2-cyclopentenone and 2-cyclohexenone, sequential three- or four-atom and then one- to three-atom ring enlargements produce nine- to 12-membered hydroxyolefinic lactones on a gram scale. 2-Cyclopentenone undergoes this serial 5 + 3 + 2 process to form 10-membered ring natural (-)-phoracantholide-J in six linear steps and 26% overall yield.
• The first stereoselective synthesis of dendrodolide A
  作者：A. Venkanna、B. Siva、B. Poornima、K. Suresh Babu、J. Madhusudana Rao

  DOI：10.1016/j.tetlet.2013.11.044

  日期：2014.1

  The first stereoselective total synthesis of natural product, dendrodolide A (1) is described from readily available (R)-propylene oxide and 3-buten-1-ol as starting materials. The synthesis was achieved in 10 steps with an overall yield of 19.1%. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification, and ring-closing metathesis (RCM). 2013 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of decarestrictine J
  作者：Partha Sarathi Chowdhury、Priti Gupta、Pradeep Kumar

  DOI：10.1016/j.tetlet.2009.10.035

  日期：2009.12

  An efficient total synthesis of decarestrictine J has been achieved using ring-closing metathesis and Yamaguchi esterification as key steps. The stereogenic centres were generated by means of iterative hydrolytic kinetic resolution (HKR) of racemic epoxides. (c) 2009 Elsevier Ltd. All rights reserved.