(S)-3-(((tert-butyldimethyl)silyl)oxy)pentanal | 105705-10-0

• 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: (S)-3-(((tert-butyldimethyl)silyl)oxy)pentanal
• 英文别名: (S)-3-((tert-butyldimethylsilyl)oxy)pentanal；(S)-3-t-butyldimethylsilyloxypentanal；(3S)-3-[tert-butyl(dimethyl)silyl]oxypentanal
• CAS: 105705-10-0
• 化学式: C₁₁H₂₄O₂Si
• 分子量: 216.396
• InChiKey: HSUANBFMJXCZPR-JTQLQIEISA-N

物化性质

• 沸点：
  231.3±23.0 °C(Predicted)
• 密度：
  0.865±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-(((tert-butyldimethyl)silyl)oxy)pentanal 在 sodium tetrahydroborate 、 cerium(III) chloride 、 氢氟酸 、 叔丁基锂 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 27.25h， 生成 (1R,3S,5R,6R)-1,8-dimethyl-3-ethyl-2,9-dioxabicyclo<3.3.1>non-7-en-6-ol
  参考文献：
  名称：

  Synthesis of both the enantiomers of the heterocyclic pheromones isolated from the male swift moth l

  摘要：

  DOI：

  10.1016/s0040-4020(01)82077-9
• 作为产物：
  描述：

  (S)-3-羟基戊腈 在 咪唑 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.0h， 生成 (S)-3-(((tert-butyldimethyl)silyl)oxy)pentanal
  参考文献：
  名称：

  Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

  摘要：

  Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the-reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomethyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.

  DOI：

  10.1021/jo971288m

文献信息

• A Designed Amide as an Aldol Donor in the Direct Catalytic Asymmetric Aldol Reaction
  作者：Karin Weidner、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1002/anie.201403118

  日期：2014.6.10

  The direct catalytic asymmetric aldol reaction offers efficient access to β‐hydroxy carbonyl entities. Described is a robust direct catalytic asymmetric aldol reaction of α‐sulfanyl 7‐azaindolinylamide, thus affording both aromatic and aliphatic β‐hydroxy amides with high ee values. The design of this transformation features a cooperative interplay of a soft and a hard Lewis acid, which together facilitate

  直接催化不对称醛醇缩合反应可高效地获得β-羟基羰基实体。描述了α-硫烷基7-氮杂吲哚基酰胺的鲁棒的直接催化不对称醛醇缩合反应，从而提供了具有高ee 值的芳族和脂族β-羟基酰胺。这种转化的设计具有软和硬路易斯酸的协同作用，它们共同促进了硬布朗斯台德碱对具有挑战性的化学选择性烯醇化作用。
• Synthesis of the Conjugated Tetraene Acid Side Chain of Mycolactone E by Suzuki-Miyaura Cross-Coupling Reaction of Alkenyl Boronates
  作者：Yuan Wang、Wei-Min Dai

  DOI：10.1002/ejoc.201301484

  日期：2014.1

  The conjugated tetraene acid side chain of mycolactone E has been synthesized by the cross-coupling reaction of a trisubstituted triene bromide with a trisubstituted alkenyl boronate catalyzed by Pd(OAc)2–Aphos-Y under mildly basic conditions [K3PO4·3H2O, H2O, tetrahydrofuran (THF), 35 °C, 18 h]. The conjugated tetraene product was obtained in 85 % yield without geometrical isomer(s) under the catalytic

  在弱碱性条件 [K3PO4·3H2O, H2O,四氢呋喃 (THF)，35 °C，18 小时]。在催化条件下，共轭四烯产物以 85% 的产率获得，不含几何异构体。这些结果表明，由 Pd(OAc)2–Aphos-Y 催化的烯基卤化物与烯基硼酸酯的偶联与 CuI 催化的区域选择性和立体选择性炔烃硼酸化相结合，为获得共轭多烯分子提供了一种有效的合成工具。
• Enantio- and Diastereoselective Synthesis of 1,5-<i>syn</i>-(<i>Z</i>)-Amino Alcohols via Imine Double Allylboration: Synthesis of <i>trans</i>-1,2,3,6-Tetrahydropyridines and Total Synthesis of Andrachcine
  作者：Christophe Allais、William R. Roush

  DOI：10.1021/acs.orglett.7b00995

  日期：2017.5.19

  A stereoselective synthesis of trans-1,2,3,6-tetrahydropyridines 8 is described. This synthesis proceeds via intramolecular Mistunobu reactions of 1,5-syn-(Z)-amino alcohols 7, which were prepared by a highly diastereo- and enantioselective double-allylboration reaction of aldehyde 5 and silylimine 6. The chiral bifunctional γ-borylallylborane 9E was generated in situ by hydroboration of allene 3 with

  描述了反式-1,2,3,6-四氢吡啶8的立体选择性合成。这种合成经由1,5-分子内Mistunobu反应所得顺式（ - Ž） -氨基醇7，其通过醛的高度diastereo-和不对称双allylboration反应制备5和silylimine 6。手性双官能γ-borylallylborane 9 Ë由丙二烯的硼氢化原位产生3与（diisopinocampheyl）硼烷4。该策略已应用于雄激素1的全合成，因此可以确定天然产品的绝对和相对构型。
• Isolation, Structure Elucidation, Biosynthesis, and Synthesis of Antalid, a Secondary Metabolite from <i>Polyangium species</i>
  作者：Thomas Tautz、Judith Hoffmann、Thomas Hoffmann、Heinrich Steinmetz、Peter Washausen、Brigitte Kunze、Volker Huch、Andreas Kitsche、Hans Reichenbach、Gerhard Höfle、Rolf Müller、Markus Kalesse

  DOI：10.1021/acs.orglett.6b00810

  日期：2016.6.3

  The isolation, structure elucidation, and synthesis of antalid (1), a novel secondary metabolite from Polyangium sp., is described herein. The structure elucidation of 1 was performed with the aid of mass spectrometry, high field NMR experiments, and crystal structure analysis. The absolute configuration of antalid was confirmed through the Mosher ester method and ultimately by total synthesis. In

  本文描述了Antalid（1）的分离，结构阐明和合成，Antalid（1）是一种来自Polyangium sp。的新型次生代谢产物。的结构说明1用质谱法，高场NMR实验，以及晶体结构分析的帮助下执行。通过Mosher酯法，并最终通过全合成，确认了Antalid的绝对构型。另外，通过对其生物合成基因簇的计算机分析，揭示了该杂种PKS-NRPS天然产物的生物合成来源。
• Total synthesis of the (+)-pheromone of the male swift moth L.
  作者：Philip DeShong、Ming-Teh Lin、Joseph J Perez

  DOI：10.1016/s0040-4039(00)84456-1

  日期：1986.1