(R)-3-(tert-butyldimethylsiloxy)tetradecanal | 137306-82-2

• 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: (R)-3-(tert-butyldimethylsiloxy)tetradecanal
• 英文别名: (R)-3-(tert-butyldimethylsilyloxy)tetradecanal；(R)-3-<(tert-butyl)dimethylsilyloxy>tetradecanal；(R)-3-(tert-bytyldimethylsilyloxy)tetradecanal；(R)-3-(tert-butyl-dimethyl-silanyloxy)-tetradecanal；(R)-3-tert-butyl dimethylsilaneoxy tetradecyl aldehyde；(R)-3-(t-butyl-dimethylsiloxy)tetradecanal；(3R)-3-[tert-butyl(dimethyl)silyl]oxytetradecanal
• CAS: 137306-82-2
• 化学式: C₂₀H₄₂O₂Si
• 分子量: 342.638
• InChiKey: PIQPQYDHYCTWIZ-LJQANCHMSA-N

物化性质

• 沸点：
  383.5±25.0 °C(Predicted)
• 密度：
  0.859±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  (R)-3-(tert-butyldimethylsiloxy)tetradecanal 在 偶氮二甲酸二异丙酯 、 氢氟酸 、 三苯基膦 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 67.0h， 生成 奥利司他
  参考文献：
  名称：

  Total Synthesis and Comparative Analysis of Orlistat, Valilactone, and a Transposed Orlistat Derivative:  Inhibitors of Fatty Acid Synthase

  摘要：

  Concise syntheses of orlistat ( Xenical), a two-carbon transposed orlistat derivative, and valilactone are described that employ the tandem Mukaiyama aldol-lactonization (TMAL) process as a key step. This process allows facile modification of the alpha-side chain. Versatile strategies for modifying the delta-side chain are described, involving cuprate addition and olefin metathesis. Comparative antagonistic activity of these derivatives toward a recombinant form of the thioesterase domain of fatty acid synthase is reported along with comparative activity-based profiling.

  DOI：

  10.1021/ol061651o
• 作为产物：
  描述：

  3-氧代十四酸乙酯 在 二异丁基氢化铝 作用下， 生成 (R)-3-(tert-butyldimethylsiloxy)tetradecanal
  参考文献：
  名称：

  Total Synthesis and Comparative Analysis of Orlistat, Valilactone, and a Transposed Orlistat Derivative:  Inhibitors of Fatty Acid Synthase

  摘要：

  Concise syntheses of orlistat ( Xenical), a two-carbon transposed orlistat derivative, and valilactone are described that employ the tandem Mukaiyama aldol-lactonization (TMAL) process as a key step. This process allows facile modification of the alpha-side chain. Versatile strategies for modifying the delta-side chain are described, involving cuprate addition and olefin metathesis. Comparative antagonistic activity of these derivatives toward a recombinant form of the thioesterase domain of fatty acid synthase is reported along with comparative activity-based profiling.

  DOI：

  10.1021/ol061651o

文献信息

• Diastereoselective allylations and crotylations under phase-transfer conditions using trifluoroborate salts: an application to the total synthesis of (−)-tetrahydrolipstatin
  作者：Avinash N Thadani、Robert A Batey

  DOI：10.1016/j.tetlet.2003.09.053

  日期：2003.10

  A mild protocol for diastereoselective allylations and crotylations of α- and β-silyloxy substituted aldehydes utilizing potassium allyl/crotyltrifluoroborates is described. The reactions proceed to completion within 30 min at room temperature in biphasic or aqueous media in the presence of a phase transfer catalyst. The resulting homoallylic alcohols are obtained in high yields and moderate to excellent

  描述了使用烯丙基/巴豆基三氟硼酸钾对α-和β-甲硅烷氧基取代的醛进行非对映选择性烯丙基化和丁烯酰化的温和方案。在相转移催化剂的存在下，在室温下在双相或水性介质中，反应在30分钟内完成。以高收率和中等至极好的非对映选择性获得所得的均烯丙基醇。该方法用于抗肥胖药四氢脂肪抑素（orlistat™）的不对称全合成。
• [EN] COMPOUNDS FOR THE REDUCING LIPOTOXIC DAMAGE<br/>[FR] COMPOSÉS POUR LA RÉDUCTION DE LÉSIONS LIPOTOXIQUES
  申请人：MAYO FOUND MEDICAL EDUCATION & RES

  公开号：WO2019014434A1

  公开（公告）日：2019-01-17

  Provided herein are novel lipase inhibitors and methods for using the same to treat inflammation, multisystem organ failure, necrotic pancreatic acinar cell death, acute pancreatitis, sepsis (e.g., culture negative sepsis), burns, and acne. For example, provided herein are two novel lipase inhibitors useful in the methods described herein: (I) (II) or a pharmaceutically acceptable salt thereof.

  本文提供了新型脂肪酶抑制剂以及使用这些抑制剂治疗炎症、多系统器官衰竭、坏死性胰腺腺泡细胞死亡、急性胰腺炎、败血症（如无菌性败血症）、烧伤和痤疮的方法。例如，本文提供了两种在本文描述的方法中有用的新型脂肪酶抑制剂：（I）（II）或其药用可接受的盐。
• An Asymmetric Synthesis of (-)-Tetrahydrolipstatin
  作者：Agnès Pommier、Jean-Marc Pons、Philip J. Kocienski、Loretta Wong

  DOI：10.1055/s-1994-25684

  日期：——

  A key step in a short asymmetric synthesis of the potent pancreatic lipase inhibitor (-)-tetrahydrolipstatin (2) is a Lewis acid-catalysed [2+2] cycloaddition of n-hexyl(trimethylsilyl)ketene (5) to (R) -3-(tert-butyldimethylsilyloxy)tetradecanal (4a).

  一种有效的胰脂肪酶抑制剂（-）-四氢脂肪酸酯（2）短链不对称合成中的关键步骤是n-己基（ trimethylsilyl）酮烯（5）与（R）-3-（叔丁基二甲基硅氧基）十四烷醛（4a）进行路易斯酸催化的[2+2]环加成反应。
• Development of an Activity-Based Probe and In Silico Design Reveal Highly Selective Inhibitors for Diacylglycerol Lipase-α in Brain
  作者：Marc P. Baggelaar、Freek J. Janssen、Annelot C. M. van Esbroeck、Hans den Dulk、Marco Allarà、Sascha Hoogendoorn、Ross McGuire、Bogdan I. Florea、Nico Meeuwenoord、Hans van den Elst、Gijsbert A. van der Marel、Jaap Brouwer、Vincenzo Di Marzo、Herman S. Overkleeft、Mario van der Stelt

  DOI：10.1002/anie.201306295

  日期：2013.11.11

  A model method: A strategy that combines a knowledge‐based in silico design approach and the development of novel activity‐based probes (ABPs) for the detection of endogenous diacylglycerol lipase‐α (DAGL‐α) is presented. This approach resulted in the rapid identification of new DAGL‐α inhibitors with high selectivity in the brain proteome. ABPP=activity‐based protein profiling.

  一种模型方法：提出了一种策略，该策略结合了基于知识的计算机设计方法和新的基于活动的探针（ABP）的开发，用于检测内源性二酰基甘油脂肪酶-α（DAGL-α）。这种方法可以快速鉴定出在脑蛋白质组中具有高选择性的新型DAGL-α抑制剂。ABPP =基于活性的蛋白质谱。
• Stereoselective Syntheses of Tetrahydroesterastin-? -Lactam Analogues
  作者：Isabelle Huber、Fernand Schneider

  DOI：10.1002/hlca.19940770420

  日期：1994.6.29

  A total synthesis of the optically active tetrahydroesterastin β -lactam analogue 2 using Miller's hydroxamate approach is described (Scheme 2). Significant modification of published procedures has resulted in a short and facile stereospecific preparation of the N-[(benzyloxycarbonyl)methyl]-β -lactam 17 starting from the readily available D-serine. This material served as intermediate for the preparation

  描述了使用米勒异羟肟酸酯方法的旋光性四氢酯弹性蛋白β-内酰胺类似物2的全合成（方案2）。已公开方法的显着改进导致从容易获得的D-丝氨酸开始的N -[（（苄氧羰基）甲基]-β-内酰胺17的短而简便的立体定向制备。该物质用作制备各种N -[（苄氧基羰基）甲基]四氢酯弹性蛋白β-内酰胺类似物的中间体（方案5）。