{[1-(benzyloxy)vinyl]oxy}(tert-butyl)dimethylsilane | 92144-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {[1-(benzyloxy)vinyl]oxy}(tert-butyl)dimethylsilane
• 英文别名: 1-t-butyldimethylsiloxy-1-benzyloxyethylene；1-tert-butyl-dimethylsiloxy-1-benzyloxyethylene；Silane, (1,1-dimethylethyl)dimethyl[[1-(phenylmethoxy)ethenyl]oxy]-；tert-butyl-dimethyl-(1-phenylmethoxyethenoxy)silane
• CAS: 92144-04-2
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: FJXSYACZPHYAPE-UHFFFAOYSA-N

物化性质

• 沸点：
  299.8±33.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  {[1-(benzyloxy)vinyl]oxy}(tert-butyl)dimethylsilane 在 palladium dihydroxide 氢气 、 zinc dibromide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.33h， 生成 (S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-{(2R,3S,5R,6S)-6-[2-(tert-butyl-dimethyl-silanyloxy)-3-carboxy-2-methyl-propyl]-3,5-dihydroxy-2-methyl-tetrahydro-pyran-2-yl}-4-methyl-pentanoic acid
  参考文献：
  名称：

  Total Synthesis of Brevetoxin A: Part 1: First Generation Strategy and Construction of BCD Ring System

  摘要：

  Discussed herein is our first generation strategy for the total synthesis of brevetoxin A. This approach relies upon dissection of the molecule at the nine-membered ring site (ring E), A Wittig coupling of requisite polycyclic fragments 3 and 4 followed by hydroxy dithioketal cyclization was expected to furnish the polycyclic framework of brevetoxin A (1). Intermediate 8 was anticipated to be a valid synthetic precursor to phosphonium salt 3, and its synthesis was accomplished by a bis(lactonization)/thionolactone formation/functionalization sequence. In order to test our synthetic strategy, the synthesis of an advanced model system (36) was attempted. Aldehyde 38 and phosphonium salt 37 were successfully synthesized and coupled through a:Wittig reaction. Unfortunately, the planned hydroxy dithioketal cyclization to form the crucial nonacene (ring E) did not proceed as anticipated and this synthetic approach was discontinued.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<599::aid-chem599>3.0.co;2-n
• 作为试剂：
  描述：

  {[1-(benzyloxy)vinyl]oxy}(tert-butyl)dimethylsilane 、 (R)-3-(4-methoxybenzyloxy)tetradecanal 在 {[1-(benzyloxy)vinyl]oxy}(tert-butyl)dimethylsilane 作用下， 以87的产率得到benzyl (3S,5R)-5-(4-methoxybenzyloxy)-3-hydroxyhexadecanoate
  参考文献：
  名称：

  J. Org. Chem. 2012, 77, 4885-4901

  摘要：

  DOI：

文献信息

• Non-metal Lewis acid-catalyzed cross-Claisen condensation for β-keto esters
  作者：Tianyu Zhang、Zhenkun Yang、Dapeng Zhou、Fuliang Meng、Zhengyu Han、Hai Huang

  DOI：10.1039/d1ob01785c

  日期：——

  In this work, we disclose a new catalytic and highly chemoselective cross-Claisen condensation of esters. In the presence of TBSNTf2 as a non-metal Lewis acid, various esters can undergo cross-Claisen condensation to form β-keto esters which are important building blocks. Compared with the traditional Claisen condensation, this process, employing silyl ketene acetals (SKAs) as carbonic nucleophiles

  在这项工作中，我们公开了一种新的催化和高度化学选择性的酯交叉克莱森缩合。在作为非金属路易斯酸的 TBSNTf 2存在下，各种酯可以进行交叉克莱森缩合以形成β-酮酯，这是重要的结构单元。与传统的克莱森缩合相比，该工艺以甲硅烷基乙烯酮缩醛（SKAs）为含碳亲核试剂实现交叉克莱森缩合，条件温和，官能团耐受性好。
• Synthesis of medium-sized ring ethers from thionolactones. Applications to polyether synthesis
  作者：K. C. Nicolaou、D. G. McGarry、P. K. Somers、B. H. Kim、W. W. Ogilvie、G. Yiannikouros、C. V. C. Prasad、C. A. Veale、R. R. Hark

  DOI：10.1021/ja00173a013

  日期：1990.8

  Reductive desulfurization using triphenyltin hydride under radical conditions afforded the corresponding cyclic ethers rapidly and efficiently and, in most cases, with complete stereocontrol. This methodology has been proven through the construction of model systems of rings B and D of brevetoxin A (1) and a synthesis of (±)-lauthisan

  已经制备了多种中等大小的硫代内酯，并与亲核试剂缩合，在用甲基碘淬灭后得到烷基化硫代缩醛。在自由基条件下使用三苯基氢化锡进行还原脱硫可以快速有效地提供相应的环醚，并且在大多数情况下具有完全立体控制。该方法已通过构建短杆菌毒素 A (1) 的 B 环和 D 环模型系统以及 (±)-lauthisan 的合成得到证明
• Stereoselective β-<i>C</i>- and β-<i>S</i>-Glycosylation of 2-Deoxyribofuranose Derivatives Controlled by the 3-Hydroxy Protective Group
  作者：Yuh-ichiro Ichikawa、Hideki Kubota、Ken’ichi Fujita、Tatsuo Okauchi、Koichi Narasaka

  DOI：10.1246/bcsj.62.845

  日期：1989.3

  β-C-2-Deoxyribofuranosides and β-S-2-deoxyribofuranosides are prepared stereoselectively from 1-O-acetyl-5-O-benzyl-3-O-[2-(methylsulfinyl)ethyl]-2-deoxy-d-erythro-pentofuranose or the corresponding 3-O-(2-pyridyl-methyl)pentofuranose N-oxide by the reaction with silyl enol ethers or trimethlsilyl sulfides in the presence of a Lewis acid.

  β-C-2-脱氧核糖苷和β-S-2-脱氧核糖苷是通过与硅乙烯醚或三甲基硅基硫化物在路易斯酸存在下反应，从1-O-乙酰基-5-O-苄基-3-O-[2-(甲基亚砜基)乙基]-2-脱氧-d-赤藓糖和相应的3-O-(2-吡啶基-甲基)五碳呋喃糖N-氧化物立体选择性制备的。
• Can a Ketone Be More Reactive than an Aldehyde? Catalytic Asymmetric Synthesis of Substituted Tetrahydrofurans
  作者：Sunggi Lee、Han Yong Bae、Benjamin List

  DOI：10.1002/anie.201806312

  日期：2018.9.10

  O‐heterocycles bearing tetrasubstituted stereogenic centers are prepared via catalytic chemo‐ and enantioselective nucleophilic additions to ketoaldehydes, in which the ketone reacts preferentially over the aldehyde. Five‐ and six‐membered rings with both aromatic and aliphatic substituents, as well as an alkynyl substituent, are obtained. Moreover, 2,2,5‐trisubstituted and 2,2,5,5‐tetrasubstituted

  带有四取代立体异构中心的O杂环是通过催化化学和对映选择性亲核性加成至酮醛而制备的，其中酮优先于醛反应。获得具有芳族和脂族取代基以及炔基取代基的五元和六元环。此外，合成的2,2,5-三取代和2,2,5,5-四取代的四氢呋喃具有出色的立体选择性。此外，脱水harringtonine侧链的三步合成证明了上述方法的合成效用。
• A New Efficient Method for Stereoselective Synthesis of 2-Deoxy-C-ribofuranosides
  作者：Teruaki Mukaiyama、Hiromi Uchiro、Noriyuki Hirano、Tatsuya Ishikawa

  DOI：10.1246/cl.1996.629

  日期：1996.8

  Stereoselective C-glycosylation of 2-deoxyribose derivatives having 3-O-thiocarbamoyl directing group with carbon nucleophiles was successfully carried out by using SiCl(OTf)3 as an activator. Several 2-deoxy-β-C-ribofuranosides which can be easily converted to 2′-deoxy-C-nucleosides were obtained in good yields with high stereoselectivities.

  成功地通过使用SiCl(OTf)3作为活化剂，对具有3-O-硫氨基甲酰基导向基的2-脱氧核糖衍生物进行了立体选择性的C-糖苷化反应，使用了碳亲核试剂。获得了几种2-脱氧-β-C-核糖呋喃苷，具有良好的产率和高的立体选择性，这些产物可以很容易转化为2′-脱氧-C-核苷。