dipropan-2-yl (4S,5S)-2-[(E)-3-[dimethyl(phenyl)silyl]prop-2-enyl]-1,3,2-dioxaborolane-4,5-dicarboxylate | 133321-83-2

• 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: dipropan-2-yl (4S,5S)-2-[(E)-3-[dimethyl(phenyl)silyl]prop-2-enyl]-1,3,2-dioxaborolane-4,5-dicarboxylate
• CAS: 133321-83-2
• 化学式: C₂₁H₃₁BO₆Si
• 分子量: 418.37
• InChiKey: HSADFBCDUPNVEH-DTVHYBFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dipropan-2-yl (4S,5S)-2-[(E)-3-[dimethyl(phenyl)silyl]prop-2-enyl]-1,3,2-dioxaborolane-4,5-dicarboxylate 在 4 A molecular sieve 作用下， 以 吡啶 、 甲苯 为溶剂， 生成 Acetic acid (1S,2R)-1-((2R,3S)-3-benzyloxymethyl-oxiranyl)-2-(dimethyl-phenyl-silanyl)-but-3-enyl ester
  参考文献：
  名称：

  酒石酸二异丙酯（E）-γ-（二甲基苯基甲硅烷基）烯丙基硼酸酯，用于从醛类对映选择性合成2-丁烯-1,4-二醇的手性烯丙基醇β-碳负离子等价物

  摘要：

  描述了4-取代的（E）-2-丁烯-1,4-二醇的对映选择性合成。该方法涉及醛与手性PhMe 2 Si-取代的烯丙基硼酸酯3的反应，然后环氧化（二甲基二环氧乙烷）和酸催化的中间环氧硅烷醇的彼得森重排。

  DOI：

  10.1016/s0040-4039(00)97300-3

文献信息

• Total Synthesis of Amphidinolide E
  作者：Porino Va、William R. Roush

  DOI：10.1021/ja066663j

  日期：2006.12.1

  A convergent and highly stereocontrolled synthesis of amphidinolide E (1) has been accomplished. The synthesis features a highly diastereoselective (>20:1) BF3.Et2O promoted [3+2] annulation reaction between aldehyde 3 and allylsilane 4 to afford substituted tetrahydrofuran 2.

  已经完成了amphidinolide E (1) 的聚合和高度立体控制的合成。该合成具有高度非对映选择性 (>20:1) BF3.Et2O 促进醛 3 和烯丙基硅烷 4 之间的 [3+2] 环化反应，得到取代的四氢呋喃 2。
• Diisopropyl tartrate modified (E)-γ-[(cyclohexyloxy)dimethylsilyl]- and (E)-γ-(dimethylphenylsilyl)allylboronates: Chiral Reagents for the Enantio- and Diastereoselective synthesis of anti 1,2-diols and 2-butene-1,4-diols via the formal α- and γ-hydroxyallylation of aldehydes
  作者：William R. Roush、Paul T. Grover

  DOI：10.1016/s0040-4020(01)88869-4

  日期：1992.1

  Enantioselective synthesis of 4-substituted (E)-2-butene-1,4-diols and anti 1,2-diols are described. Highly diastereoselective reactions of aldehydes and the chiral PhMe2Si- and (C6H11O)Me2Si- substituted allylboronates 25 and 26 provide anti homoallylic 29 and 50, respectively. Epoxidation of 29 with dimethyl dioxirane followed by acid catalyzed Petersen rearrangement of the intermediate epoxysilanols

  描述了4-取代的（E）-2-丁烯-1,4-二醇和抗1,2-二醇的对映选择性合成。醛与手性PhMe 2 Si-和（C 6 H 11 O）Me 2 Si-取代的烯丙基硼酸酯25和26的高度非对映选择性反应分别提供反均聚物29和50。29用二甲基二环氧乙烷环氧化，然后经酸催化的中间体环氧硅烷醇进行Petersen重排，可得到具有优异对映选择性（81-87％ee）的1,4-丁二醇27。Tamao氧化50提供抗二醇22（ee的64–72％）。这些程序尤其在与一系列氧化的手性醛进行双不对称反应时获得了优异的结果（图1和2）。这些方法有望用于非环状前体糖的非对映选择性合成中。
• Total synthesis of amphidinolide E and amphidinolide E stereoisomers
  作者：Porino Va、William R. Roush

  DOI：10.1016/j.tet.2007.02.058

  日期：2007.6

  Four amphidinolide E stereoisomers, amphidinolide E (1), 2-epi-amphidinolide E (2), 19-epi-amphidinolide E (3), and 2-epi-19-epi- amphidinolide E (4), have been synthesized via the judicious union of aldehyde 5, allylsilanes 7 or 8, acids 9 or 10, and vinylstannane 6. The C19 stereocenters of the C19 epimeric allylsilanes 7 and 8 were introduced via crotylboration reactions early in the synthesis. [3+2] Annulation reactions of aldehyde 5 with allylsilanes 7 and 8 were employed to set the core tetrahydrofuran units of 1-4. Finally, the C2 stereo-center was installed by esterification using acid 9, without incident, or with acid 10, in which case an unexpected and completely stereoselective inversion of C2 occurs. (C) 2007 Elsevier Ltd. All rights reserved.
• Diisopropyl tartrate (E)-γ-(dimethylphenylsilyl)allylboronate, a chiral allylic alcohol β-carbanion equivalent for the enantioselective synthesis of 2-butene-1,4-diols from aldehydes
  作者：William R. Roush、Paul T. Grover

  DOI：10.1016/s0040-4039(00)97300-3

  日期：1990.1

  An enantioselective synthesis of 4-substituted (E)-2-buten-1,4-diols is described. The method involves the reaction of aldehydes with the chiral PhMe2Si- substituted allylboronate3 followed by epoxidation (dimethyl dioxirane) and acid catalyzed Petersen rearrangement of the intermediate epoxysilanols.

  描述了4-取代的（E）-2-丁烯-1,4-二醇的对映选择性合成。该方法涉及醛与手性PhMe 2 Si-取代的烯丙基硼酸酯3的反应，然后环氧化（二甲基二环氧乙烷）和酸催化的中间环氧硅烷醇的彼得森重排。