(R)-3-(tert-butyldimethylsilanyloxy)hexadecanal | 945736-86-7

• 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-butyldimethylsilanyloxy)hexadecanal
• 英文别名: (3R)-3-[tert-butyl(dimethyl)silyl]oxyhexadecanal
• CAS: 945736-86-7
• 化学式: C₂₂H₄₆O₂Si
• 分子量: 370.692
• InChiKey: KTFFGRMJVZDBGO-OAQYLSRUSA-N

物化性质

• 沸点：
  412.5±28.0 °C(Predicted)
• 密度：
  0.858±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  25
• 可旋转键数：
  17
• 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-butyldimethylsilanyloxy)hexadecanal 在 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.83h， 生成 (2S,4S,6R)-2-[2-(4-hydroxyphenyl)ethyl]-2-methoxy-6-tridecyltetrahydropyran-4-ol
  参考文献：
  名称：

  Diastereodivergent Strategies for the Synthesis of Homochiral Aculeatins

  摘要：

  We report concise and stereocontrolled syntheses of aculeatins (-)-A, (+)-B, (+)-D, and (+)-6-epi-D. Diastereodivergent 1,3-inductions in Mukaiyama aldol coupling contribute to reduce steps and to increase flexibility with reactants having sterically restricted proximal substituents (i.e., CH2), involving either a good anti or a moderate syn 1,3-induction, depending on the nature of protecting group (P). In addition, the 3,5-syn-diol-ketone resulting from concomitant deprotection of the beta-alkoxy (Tr = trityl) group proves to be remarkably stable whereas the 3,5-anti diastereoisomer cyclizes spontaneously to the corresponding tetrahydropyran hemiketal, thus enabling a useful and facile separation. The second part of our study is devoted to improving the yield and the diastereoselectivity of the final phenolic oxidation reaction leading to aculeatins.

  DOI：

  10.1021/jo0707986
• 作为产物：
  描述：

  (2E,5R)-octadec-2-en-5-ol 在 咪唑 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 2.25h， 生成 (R)-3-(tert-butyldimethylsilanyloxy)hexadecanal
  参考文献：
  名称：

  Diastereodivergent Strategies for the Synthesis of Homochiral Aculeatins

  摘要：

  We report concise and stereocontrolled syntheses of aculeatins (-)-A, (+)-B, (+)-D, and (+)-6-epi-D. Diastereodivergent 1,3-inductions in Mukaiyama aldol coupling contribute to reduce steps and to increase flexibility with reactants having sterically restricted proximal substituents (i.e., CH2), involving either a good anti or a moderate syn 1,3-induction, depending on the nature of protecting group (P). In addition, the 3,5-syn-diol-ketone resulting from concomitant deprotection of the beta-alkoxy (Tr = trityl) group proves to be remarkably stable whereas the 3,5-anti diastereoisomer cyclizes spontaneously to the corresponding tetrahydropyran hemiketal, thus enabling a useful and facile separation. The second part of our study is devoted to improving the yield and the diastereoselectivity of the final phenolic oxidation reaction leading to aculeatins.

  DOI：

  10.1021/jo0707986

文献信息

• Total Synthesis of Aculeatins A, B and D and 6-epi-Aculeatin D via an Asymmetric­ Aldol Approach
  作者：Biswanath Das、Lingaiah Maram

  DOI：10.1055/s-0033-1340866

  日期：——

  Abstract Simple and efficient stereoselective total syntheses of aculeatins A, B and D and 6-epi-aculeatin D starting from 1-tetradecanal have been accomplished. The synthesis is based on the Crimmins aldol reaction involving a chiral auxiliary. Simple and efficient stereoselective total syntheses of aculeatins A, B and D and 6-epi-aculeatin D starting from 1-tetradecanal have been accomplished. The

  摘要 从1-四癸醛开始的aculeatins A，B和D和6- epi - aculeatin D的简单，有效的立体选择性总合成已经完成。该合成基于涉及手性助剂的Crimmins aldol反应。 从1-四癸醛开始的aculeatins A，B和D和6- epi - aculeatin D的简单，有效的立体选择性总合成已经完成。该合成基于涉及手性助剂的Crimmins aldol反应。
• BETA-LACTONE COMPOUNDS
  申请人：Smith Jeffrey W.

  公开号：US20090124681A1

  公开（公告）日：2009-05-14

  The present invention provides compounds having the general structure A, or a pharmaceutically acceptable derivatives thereof: wherein R is an alkyl group, and R 1 comprises at least one moiety selected from a group consisting of an alkyl, an alkenyl, an aryl, a heterocycle, hydroxyl, ester, amido, aldehyde, and a halogen.

  本发明提供具有一般结构A的化合物，或其药学上可接受的衍生物：其中R是烷基基团，R1包括至少一种从烷基、烯基、芳基、杂环、羟基、酯、酰胺、醛基和卤素组成的基团。
• 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.
• An efficient and stereoselective route to 1-deoxy-5-hydroxy sphingosine analogues
  作者：Partha Pratim Saikia、Abhishek Goswami、Gakul Baishya、Nabin C. Barua

  DOI：10.1016/j.tetlet.2009.01.024

  日期：2009.3

  A short and efficient synthesis of 1-deoxy-5-hydroxy sphingolipid is described. The key steps involved are a Jacobsen hydrolytic kinetic resolution (HKR) and Shibasaki's asymmetric Henry reaction. (C) 2009 Elsevier Ltd. All rights reserved.