(2S,4R)-2,4-dimethyl-5-(tosyloxy)pentyl acetate | 176900-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4R)-2,4-dimethyl-5-(tosyloxy)pentyl acetate
• 英文别名: (2S,4R)-2,4-dimethyl-5-{[(4-methylphenyl)sulfonyl]oxy}pentyl acetate；[(2S,4R)-2,4-dimethyl-5-(4-methylphenyl)sulfonyloxypentyl] acetate
• CAS: 176900-61-1
• 化学式: C₁₆H₂₄O₅S
• 分子量: 328.43
• InChiKey: ZQHNDXQNMTVXIG-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2,4-dimethyl-5-(tosyloxy)pentyl acetate 在 lithium aluminium tetrahydride 、 四溴化碳 、 magnesium 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (3R)-3,5-dimethylhexan-1-ol
  参考文献：
  名称：

  Enzymatic synthesis of (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale

  摘要：

  The sex pheromone of Matsucoccus matsumurae Japanese pine bast scale (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (1) was synthesized with stereocontrol from (2R,4S)-5-acetoxy 2,4-dimethyl-pentanol (3), which in turn was prepared by lipase-catalyzed transesterification of meso-2,4-dimethyl-1,5-propanediol (2). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00014-4
• 作为产物：
  描述：

  顺式-3,5-二甲基二氢-2H-吡喃-2,6(3H)-二酮 在 吡啶 、 lithium aluminium tetrahydride 、 amano lipase AK from pseudomonas fluorescens 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 50.5h， 生成 (2S,4R)-2,4-dimethyl-5-(tosyloxy)pentyl acetate
  参考文献：
  名称：

  DAT2 的不对称全合成和结构修正，DAT2 是一种来自结核分枝杆菌的抗原糖脂

  摘要：

  结核分枝杆菌的重要抗原 DAT2 的 4 种立体异构体的不对称合成表明，必须校正 DAT2 及其酰基取代基霉菌皮酸的普遍接受的结构。DAT2 是一种有效的配体，可激活 Mincle，Mincle 是免疫系统的重要模式识别受体。

  DOI：

  10.1002/anie.202318582

文献信息

• Enantioselective Total Synthesis of the Unnatural and the Natural Stereoisomers of Vittatalactone
  作者：Yvonne Schmidt、Konrad Lehr、Ulrich Breuninger、Gabriel Brand、Tomislav Reiss、Bernhard Breit

  DOI：10.1021/jo100383u

  日期：2010.7.2

  of the cucumber beetle. In this context, we developed the asymmetric total synthesis of the aggregation pheromone of A. vittatum, Vittatalactone, to determine its absolute configuration and to further examine the pheromone response in field studies. The synthesis features an enzyme-catalyzed approach toward the deoxypropionate structural motif. A preformed organocopper reagent could then be coupled in

  条纹黄瓜甲虫Acalymma vittatum是造成北美葫芦作物严重受损的原因。为了制定对环境无害的植物保护策略，最近的研究集中在鉴定黄瓜甲虫的性信息素。在这种情况下，我们开发了A. vittatum的聚集信息素的不对称全合成，Vittatalactone，以确定其绝对构型，并在野外研究中进一步检查了信息素的反应。合成的特征是通过酶催化的方法实现脱氧丙酸酯的结构基序。预成型有机铜试剂然后可以在被耦合的对映选择性ö -DPPB定向烯丙基取代与官能ö-DPPB-酯。通过这种有效的转化，可以在高度收敛的合成过程中获得维他他内酯。
• METHOD FOR PREPARING VITTATALACTONE
  申请人：BREIT Bernhard

  公开号：US20110282075A1

  公开（公告）日：2011-11-17

  The present invention relates to the chemical synthesis of vittatalactone, the aggregation pheromone of the striped cucumber beetle, Acalymma vittatum.

  本发明涉及条纹黄瓜甲（Acalymma vittatum）聚集信息素vittatalactone的化学合成。
• Total Synthesis and Antimicrobial Activity of Tumescenamide C and Its Derivatives
  作者：Nobuaki Takahashi、Kensuke Kaneko、Hideaki Kakeya

  DOI：10.1021/acs.joc.9b03516

  日期：2020.3.20

  C (1) is an antimicrobial compound produced by Streptomyces sp. KUSC_F05 and consists of a cyclic depsipeptide core and a polyketide side chain with branched methyl groups. Here, we report the total synthesis of tumescenamide C and two derivatives, mainly using Fmoc solid-phase peptide synthesis (SPPS). In addition, a biological evaluation of these compounds revealed the critical partial structure

  Tumescenamide C（1）是由链霉菌属（Streptomyces sp。）生产的一种抗菌化合物。KUSC_F05由环状二肽核心和带有分支甲基的聚酮侧链组成。在这里，我们报告了图梅净胺C和两种衍生物的总合成，主要使用Fmoc固相肽合成（SPPS）。此外，对这些化合物的生物学评估显示出抗菌活性中关键的部分结构。
• Synthesis of (2R,4R)-Supellapyrone, the Sex Pheromone of the Brownbanded Cockroach,Supella longipalpa, and Its Three Stereoisomers
  作者：Ken Fujita、Kenji Mori

  DOI：10.1002/1099-0690(200102)2001:3<493::aid-ejoc493>3.0.co;2-b

  日期：2001.2

  Supellapyrone [(2R,4R)-5-(2,4-dimethyl)-3-methyl-2H-pyran-2-one (1)], the female sex pheromone of the brownbanded cockroach (Supella longipalpa), and its three stereoisomers were synthesized by employing Iipase-catalyzed desymmetrization or enantiomer separation of syn- or anti-2,4-dimethylpentane- 1,5-diol (9) as the key step.
• Antibodies with Broad Specificity to Azaspiracids by Use of Synthetic Haptens
  作者：Craig J. Forsyth、Jianyan Xu、Son T. Nguyen、Ingunn A. Samdal、Lyn R. Briggs、Thomas Rundberget、Morten Sandvik、Christopher O. Miles

  DOI：10.1021/ja066971h

  日期：2006.11.1

  The development of general, sensitive, portable, and quantitative assays for the azaspiracid (AZA) class of marine toxins is urgently needed. Use of a synthetic hapten containing rings F-I of AZA to generate antibodies that cross-react with the AZAs via their common C28-C40 domain and use of these antibodies in ELISA and immunoaffinity columns are reported. This approach has many advantages over using intact azaspiracids (AZAs) derived from environmental samples or total synthesis as haptens for antibody development. A derivative of the levorotatory C28-C40 azaspiracid domain (1) was synthesized efficiently using a one-pot Staudinger reduction/intramolecular aza-Wittig reaction-imine capture sequence to form the H-I ring spiroaminal and a double intramolecluar hetero-Michael addition to assemble the F-G ring ketal. Conjugation of the hapten 1 to cBSA and immunization in sheep generated antibodies that recognized and bound to ovalbumin-conjugated 1 in the absence of AZA1. This binding was inhibited by 1 in a concentration-dependent manner. A mixture of AZA1, AZA2, AZA3, and AZA6 caused a degree of inhibition of antibody binding consistent with its total AZA content, rather than just its content of AZA1. This result suggests that the antibodies also have a similar affinity for AZA2, AZA3, and AZA6 as they do for AZA1 and that such antibodies are suitable for analysis of AZAs in shellfish samples.