(S)-5-((tert-butyldimethylsilyl)oxy)pent-1-en-3-ol | 1360818-18-3

• 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)-5-((tert-butyldimethylsilyl)oxy)pent-1-en-3-ol
• 英文别名: (3S)-5-[tert-butyl(dimethyl)silyl]oxypent-1-en-3-ol
• CAS: 1360818-18-3
• 化学式: C₁₁H₂₄O₂Si
• 分子量: 216.396
• InChiKey: QYYAMQLYEVLYBH-SNVBAGLBSA-N

物化性质

• 沸点：
  251.0±28.0 °C(Predicted)
• 密度：
  0.882±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5-((tert-butyldimethylsilyl)oxy)pent-1-en-3-ol 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 (R)-5-tert-butyldimethylsilyloxypent-1-en-3-ol
  参考文献：
  名称：

  A chemoenzymatic asymmetric synthesis of (+)-strictifolione

  摘要：

  A chemoenzymatic asymmetric synthesis of the title compound has been developed using an efficient lipase-catalyzed acylation and a chiral reagent-directed diastereoselective allylation as the key steps for incorporating the stereogenic centers. A cross metathesis was employed to obtain the required E-olefin geometry of the target compound. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.015
• 作为产物：
  描述：

  3-(叔丁基二甲基硅氧)丙醇 在 sodium acetate 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 61.0h， 生成 (S)-5-((tert-butyldimethylsilyl)oxy)pent-1-en-3-ol
  参考文献：
  名称：

  A chemoenzymatic asymmetric synthesis of (+)-strictifolione

  摘要：

  A chemoenzymatic asymmetric synthesis of the title compound has been developed using an efficient lipase-catalyzed acylation and a chiral reagent-directed diastereoselective allylation as the key steps for incorporating the stereogenic centers. A cross metathesis was employed to obtain the required E-olefin geometry of the target compound. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.015

文献信息

• γ-lactones from δ-lactones: total synthesis of the biosynthetic derailment product mupirocin H
  作者：Robert W. Scott、Carlo Mazzetti、Thomas J. Simpson、Christine L. Willis

  DOI：10.1039/c2cc17721h

  日期：——

  Two different strategies for the synthesis of functionalised γ-lactones from δ-lactones are described and used in a convergent synthesis of (+)-mupirocin H. The total synthesis is versatile and may be readily adapted for the preparation of further truncated metabolites from Pseudomonas fluorescens.

  描述了两种从δ-内酯合成功能化γ-内酯的不同策略，并用于(+)-莫匹罗星H的汇聚式合成。这种全合成方法具有广泛的适用性，并可以轻松适应于从荧光假单胞菌制备其他截短的代谢产物。
• Stereoselective Total Synthesis of Bioactive Marine Natural Product Biselyngbyolide B
  作者：Sayantan Das、Debobrata Paul、Rajib Kumar Goswami

  DOI：10.1021/acs.orglett.6b00713

  日期：2016.4.15

  A convergent strategy for the stereoselective total synthesis of biologically active marine natural product biselyngbyolide B has been developed. Key strategies of this synthesis include Jamison protocol of trans-hydroalumination/allylation for installation of C18–C23 olefin moiety and intramolecular Heck coupling for macrocyclization.

  已开发出一种用于生物活性海洋天然产物比塞林比洛莱德B的立体选择性全合成的收敛策略。该合成的关键策略包括用于安装C 18 -C 23烯烃部分的反式氢铝化/烯丙基化的贾米森协议，以及用于大环化的分子内Heck偶联。
• Syntheses of Thailandepsin B Pseudo‐Natural Products: Access to New Highly Potent HDAC Inhibitors via Late‐Stage Modification
  作者：Jana Brosowsky、Monika Lutterbeck、Amelie Liebich、Manfred Keller、Daniel Herp、Anja Vogelmann、Manfred Jung、Bernhard Breit

  DOI：10.1002/chem.202002449

  日期：2020.12.9

  offers the possibility to introduce varying warheads via late stage modification. Additionally, it gives access to the asymmetric branched allylic ester moiety of the natural product in a highly diastereoselective manner applying rhodium‐catalyzed hydrooxycarbonylation. The newly developed pseudo‐natural products are extremely potent and selective HDAC inhibitors. The non‐proteinogenic amino acid d‐norleucine

  新的Thaiepsin B假天然产物已经制备。我们的综合策略提供了通过后期修改引入不同弹头的可能性。此外，它还可以通过铑催化的氢氧羰基化以非对映选择性的方式获得天然产物的不对称支链烯丙基酯部分。新开发的伪天然产物是非常有效和选择性的HDAC抑制剂。通过最近开发的铑催化加氢胺化方法，对映选择性地获得了非蛋白氨基酸的d-正亮氨酸。
• A facile chiral pool synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O
  作者：Kuchena Vamshikrishna、Garlapati Srinu、Pabbaraja Srihari

  DOI：10.1016/j.tetasy.2013.12.008

  日期：2014.2

  A facile chiral pool total synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O has been achieved from L-(+)-diethyl tartrate. The strategy utilized is conventional and flexible. Wittig homologation and Grubbs ring closing metathesis are the key reactions employed for the synthesis of the title molecules. (C) 2013 Elsevier Ltd. All rights reserved.