(3R)-3-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}octanal | 220484-17-3

• 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: (3R)-3-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}octanal
• 英文别名: (R)-(-)-3-(tert-butyl-dimethyl-silyloxy)octanal；(R)-(-)-3-(tert-butyldimethylsilyl)oxyoctanal；(R)-(-)-3-(tert-butyldimethylsilyloxy)octanal；(3R)-3-(tert-butyldimethylsiloxy)octanal；(R)-3-[(tert-butyldimethylsilyl)oxy]octanal；(3R)-3-[tert-butyl(dimethyl)silyl]oxyoctanal
• CAS: 220484-17-3
• 化学式: C₁₄H₃₀O₂Si
• 分子量: 258.476
• InChiKey: VZIGDCYEXNAETQ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (3R)-3-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}octanal 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.5h， 生成 5-羟基-2-癸烯酸-δ-内酯
  参考文献：
  名称：

  Versatile Approach for the Asymmetric Synthesis of (R)‐ and (S)‐Massoialactones

  摘要：

  DOI：

  10.1080/00397910701229107
• 作为产物：
  描述：

  (R)-3-羟基辛酸甲酯 在 2,6-二甲基吡啶 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 (3R)-3-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}octanal
  参考文献：
  名称：

  Synthesis of enantiopure (R)-(−)-massoialactone through ruthenium-SYNPHOS® asymmetric hydrogenation

  摘要：

  Total synthesis of enantiopure (R)-(-)-massoialactone was achieved. The key step includes the asymmetric hydrogenation of an achiral beta-keto ester using a ruthenium-SYNPHOS (R) catalyst to set the hydroxyl function in a stereocontrolled manner with excellent enantioselectivity (> 99% ee). Ring closing metathesis (RCM) in the presence of Grubbs' catalyst allows the final construction of the six-membered lactone. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.048

文献信息

• Total Synthesis and Absolute Configuration of Simpotentin, a Potentiator of Amphotericin B Activity
  作者：Masaki Ohtawa、Eri Shimizu、Atsushi Saito、Sayuri Sakamoto、Ai Waki、Ariko Kondo、Akiho Yagi、Ryuji Uchida、Hiroshi Tomoda、Tohru Nagamitsu

  DOI：10.1021/acs.orglett.9b01945

  日期：2019.7.19

  potentiator of amphotericin B activity against Candida albicans, was achieved. Our research results enabled the access of all stereoisomers of 1 and the elucidation of the unknown absolute configuration of 1. Furthermore, one of the stereoisomers is a better amphotericin B potentiator than 1 and is an excellent lead compound for the development of a novel amphotericin B potentiator.

  实现了辛泊汀（1）的全合成，这是一种新的两性霉素B对白色念珠菌活性的增强剂。我们的研究结果使所有的立体异构体的访问1和未知绝对构型的阐明1。此外，立体异构体之一是比1更好的两性霉素B增效剂，并且是开发新型两性霉素B增效剂的极好的先导化合物。
• A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions
  作者：Syun-ichi Kiyooka、Mostofa A. Hena

  DOI：10.1021/jo990342r

  日期：1999.7.1

  A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilization of five aldol reactions with a sequence of silyl nucleophiles, 7, 8, 35, 10, and 11, in the presence of stoichiometric amounts of the promoter, 1 or 2. The construction of the relative configuration between the stereogenic centers is diastereoselectively controlled by the stereochemistry of the promoter used in the enantioselective aldol reaction, which is nearly independent of that of the substrate (promoter control).
• Toward a practical synthesis of acutiphycin. Highly stereoselective synthesis of C10-epi seco acid derivative via reaction paths shortened by using a series of chiral oxazaborolidinone-promoted aldol reactions
  作者：Mostofa Abu Hena、Chul-Sa Kim、Michio Horiike、Syun-ichi Kiyooka

  DOI：10.1016/s0040-4039(98)02553-2

  日期：1999.2
• Synthesis of Novel β-Lactone Inhibitors of Fatty Acid Synthase
  作者：Robyn D. Richardson、Gil Ma、Yatsandra Oyola、Manuel Zancanella、Lynn M. Knowles、Piotr Cieplak、Daniel Romo、Jeffrey W. Smith

  DOI：10.1021/jm800321h

  日期：2008.9.11

  Fatty acid synthase (FAS) is necessary for growth and survival of tumor cells and is a promising drug target for oncology. Here, we report oil the syntheses and activity of novel inhibitors of the thioesterase domain of FAS. Using the structure of orlistat as a starting point, which contains a beta-lactone as the central pharmacophore, 28 novel congeners were synthesized and examined. Structural features such as the length of the alpha- and beta-alkyl chains, their chemical composition, and arnino ester substitutions were altered and tile resulting compounds explored for inhibitory activity toward the thioesterase domain of FAS. Nineteen congeners show improved potency for FAS in biochemical assays relative to orlistat. Three of that subset, including the natural product valilactone, also display all increased potency in inducing tumor cell death and improved solubility compared to orlistat. These findings Support the idea that all orlistat congener can be optimized for use in a preclinical drug design and for clinical drug development.
• The β-lactone route to α,β-unsaturated δ-lactones. Total syntheses of (±)-goniothalamin and (−)-massoialactone
  作者：Lycia Fournier、Philip Kocienski、Jean-Marc Pons

  DOI：10.1016/j.tet.2003.11.094

  日期：2004.2

  The HF-induced translactonization of 2'-silyloxy-3-trimethylsilyl-2-oxetanones, obtained through Lewis acid-promoted [2+2] cycloaddition between beta-silyloxyaldehydes and trimethylsilylsilylketene, into alpha,beta-unsaturated delta-lactones is applied to the syntheses of (+/-)-goniothalamin and (-)-massoialactone. (C) 2003 Elsevier Ltd. All rights reserved.