(4R,5R)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-hydroxymethyl-1,3-dioxolane | 169871-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-hydroxymethyl-1,3-dioxolane
• 英文别名: [(4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 169871-36-7
• 化学式: C₂₃H₃₂O₄Si
• 分子量: 400.59
• InChiKey: XMXUBCUCCBZXQX-NHCUHLMSSA-N

物化性质

• 沸点：
  456.6±33.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-hydroxymethyl-1,3-dioxolane 在 咪唑 、 正丁基锂 、 碘 、 palladium(II) hydroxide 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-(tert-butyldiphenylsiloxy)-2-butanone
  参考文献：
  名称：

  A convergent approach for the total synthesis of the α-glucosidase inhibitor (−)-panaxjapyne-C

  摘要：

  The stereoselective total synthesis of (-)-panaxjapyne-C was accomplished in a convergent fashion. The synthesis utilizes the readily available enantiomers L-(+)-diethyltartrate and D-(-)-diethyltartrate and involves a Cadiot-Chodkiewicz coupling reaction, and an Ohira-Bestmann reaction as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.017
• 作为产物：
  描述：

  (4S,5S)-2,2-二甲基-1,3-二恶茂-4,5-二甲酸二乙酯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (4R,5R)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-hydroxymethyl-1,3-dioxolane
  参考文献：
  名称：

  A convergent approach for the total synthesis of the α-glucosidase inhibitor (−)-panaxjapyne-C

  摘要：

  The stereoselective total synthesis of (-)-panaxjapyne-C was accomplished in a convergent fashion. The synthesis utilizes the readily available enantiomers L-(+)-diethyltartrate and D-(-)-diethyltartrate and involves a Cadiot-Chodkiewicz coupling reaction, and an Ohira-Bestmann reaction as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.017

文献信息

• Synthesis of Glycocinnasperimicin D
  作者：Taihei Nishiyama、Yoshifumi Kusumoto、Ken Okumura、Kanako Hara、Shohei Kusaba、Keiko Hirata、Yukihiro Kamiya、Minoru Isobe、Keiji Nakano、Hiyoshizo Kotsuki、Yoshiyasu Ichikawa

  DOI：10.1002/chem.200901745

  日期：2010.1.11

  The first total synthesis of amino sugar antibiotic glycocinnasperimicin D (1) has been achieved by a convergent, three‐component coupling strategy. The key steps involve the Heck–Mizoroki reaction by using the iodophenyl glycoside 50 and acryl amide 32 to furnish the right core structure of 1, and the construction of the urea glycoside employing the reaction of glycosyl isocyanate 8 with amino sugar

  氨基糖抗生素糖皮质激素亚胺D（1）的第一个全合成方法是通过收敛的三组分偶联策略实现的。的关键步骤涉及通过使用碘苯基糖苷赫克-Mizoroki反应50和丙烯酰胺32，得到的右侧芯结构1，并采用糖基异氰酸酯的反应的尿素糖苷的结构8与氨基糖9。通过氧化异腈10制备异氰酸糖基酯8，在偶联事件中显示出极好的反应性。在合成过程中遇到的合成障碍导致了使用2-氨基-六吡喃糖的α-选择性路易斯酸催化的苯基糖基化过程的发展，以及一种不影响甲硅烷基醚的乙酰胺脱保护的方法。
• Stereocontrolled synthesis of four isomeric linoleate triols of relevance to skin barrier formation and function
  作者：Robert W. Davis、Alexander Allweil、Jianhua Tian、Alan R. Brash、Gary A. Sulikowski

  DOI：10.1016/j.tetlet.2018.11.033

  日期：2018.12

  the mammalian skin permeability barrier. In connection with the study of their involvement in barrier formation we required access to isomerically pure and defined samples of four linoleate triol esters. A common synthetic strategy was developed starting from isomeric alkynols derived from d-tartaric acid and 2-deoxy-d-ribose.

  亚油酸酯三醇酯是沿着哺乳动物皮肤渗透性屏障形成的途径的中间体。在研究它们参与形成壁垒的过程中，我们需要获得四种亚油酸酯三醇酯的异构体纯净和确定的样品。从衍生自d-酒石酸和2-脱氧-d-核糖的异构炔醇开始发展了一种通用的合成策略。
• Synthesis of dl-cis- and (4R,5R)-trans-7-[2,2-dimethyl-4-(phenylsulfonyl)-aminomethyl-1,3-dioxolan-5-yl]-5(Z)-heptenoic acid analogues as platelet thromboxane A2 receptor antagonist
  作者：D Komiotis、S PananookoolnJ、K Zaw、JP Dieter、GC Le Breton、DL Venton

  DOI：10.1016/0223-5234(96)88240-7

  日期：1995.1

  The title compounds have been synthesized and their in vitro thromboxane A(2) (TxA(2)) receptor antagonist activity evaluated. Both cis and trans isomers (1, 2) were shown to specifically inhibit submaximal human platelet aggregation induced by 225 nM U46619 in a dose-dependent manner with an IC50 of 1 mu M. The concentration of 1 and 2 required to completely block maximal aggregation induced by 3 mu M U46619 was 3 mu(M).