(4S,5R,E)-4,6-bis(benzyloxy)hex-2-ene-1,5-diol | 904324-49-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4S,5R,E)-4,6-bis(benzyloxy)hex-2-ene-1,5-diol
• 英文别名: (E,4S,5R)-4,6-bis(phenylmethoxy)hex-2-ene-1,5-diol
• CAS: 904324-49-8
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: MEHSFFNZUSPGNW-JTPPTGOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R,E)-4,6-bis(benzyloxy)hex-2-ene-1,5-diol 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(2E)-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose
  参考文献：
  名称：

  Diastereoselective synthesis of the C29–C41 fragment of karlotoxin 2

  摘要：

  A highly diastereoselective synthesis of the C29-C41 fragment of karlotoxin 2 (KmTx2) is described by employing regio-selective epoxide opening, our own developed domino isomerization followed by C-O and C-C bond formation reaction and chelation-controlled Grignard reaction as key steps. The synthesis involves installation of seven stereocenters present in the C29-C41 fragment of karlotoxin 2. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.051
• 作为产物：
  描述：

  (E)-ethyl 3-((2R,3R)-3-(benzyloxymethyl)oxiran-2-yl)acrylate 在 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (4S,5R,E)-4,6-bis(benzyloxy)hex-2-ene-1,5-diol
  参考文献：
  名称：

  Diastereoselective synthesis of the C29–C41 fragment of karlotoxin 2

  摘要：

  A highly diastereoselective synthesis of the C29-C41 fragment of karlotoxin 2 (KmTx2) is described by employing regio-selective epoxide opening, our own developed domino isomerization followed by C-O and C-C bond formation reaction and chelation-controlled Grignard reaction as key steps. The synthesis involves installation of seven stereocenters present in the C29-C41 fragment of karlotoxin 2. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.051

文献信息

• Aglycone mimics for tuning of glycosidase inhibition: design, synthesis and biological evaluation of bicyclic pyrrolidotriazole iminosugars
  作者：Inderpreet Arora、Sandeep K. Sharma、Arun K. Shaw

  DOI：10.1039/c5ra26005a

  日期：——

  Various fuco-configured bicyclic pyrrolidotriazole aglycone mimics were synthesised using copper-catalysed coupling of allyl bromides with terminal alkynes and Sonogashira–Hagihara reaction followed by intramolecular azide-alkyne ‘click’ reaction. The mimicry of the aglycone segment tends to bring about switching of activity amongst α-glucosidases and a 10 to 14-fold enhancement in potency for α-fucosidase

  使用铜催化的烯丙基溴与末端炔烃的偶联和Sonogashira–Hagihara反应，然后进行分子内叠氮化物-炔烃的“点击”反应，合成了各种fuco构型的双环吡咯并三唑糖苷配基模拟物。糖苷配基片段的模仿趋向于引起α-葡糖苷酶之间的活性切换，并且对α-岩藻糖苷酶的抑制能力提高10至14倍。
• Design, synthesis and biological evaluation of bicyclic iminosugar hybrids: conformational constraint as an effective tool for tailoring the selectivity of α-glucosidase inhibitors
  作者：Inderpreet Arora、Vivek Kr. Kashyap、Alok Kumar Singh、Arunava Dasgupta、Brijesh Kumar、Arun K. Shaw

  DOI：10.1039/c4ob00486h

  日期：——

  Principle guided design of glycan processing enzyme inhibitors involves embedding aromatic groups onto charge and shape mimics. Intramolecular azide–alkyne cycloaddition was used as a simple and versatile strategy for the synthesis of novel condensed bicyclic triazoles from carbohydrate derived Perlin aldehydes. These newly synthesised molecules were evaluated for glycosidase inhibition against 11 commercially available enzymes and were found to possess significant affinity (micromolar range) as well as high degree of selectivity for α-glucosidases. Conformational restriction was identified as an important tool to customize the selectivity of enzyme inhibition by five-membered iminosugars.

  原理导向的糖苷处理酶抑制剂设计涉及将芳香基团嵌入电荷和形状模仿物中。使用分子内叠氮-炔烃环加成反应作为合成从碳水化合物衍生的佩林醛生成新颖的缩合双环三唑的简单而多功能的策略。这些新合成的分子被评估了对11种商业可得酶的糖苷酶抑制作用，结果发现其对α-葡萄糖苷酶具有显著的亲和力（微摩尔范围）以及较高的选择性。识别出构象限制作为定制酶抑制选择性的一个重要工具，适用于五元氮杂糖。
• Studies on epoxidation of enantiomerically pure 2,3-dideoxy hex-2-enitols: a convenient access to highly functionalized enantiomerically pure tetrahydrofuran derivatives
  作者：Ram Sagar、L. Vijaya Raghava Reddy、Arun K. Shaw

  DOI：10.1016/j.tetasy.2006.04.022

  日期：2006.4

  8–14 derived from their respective glycals with Sharpless, m-CPBA and Camp’s reagents was carried out in order to obtain 2,3-epoxy alcohols keeping in view the versatility of these synthons in synthetic chemistry for the preparation of various molecules of biological importance by suitable chemical transformations. During the course of this study, the Sharpless asymmetric epoxidation reaction was found

  上对映体纯的烯丙醇的环氧化的详细比较研究8 - 14从与夏普勒斯，其各自衍生烯糖米-CPBA和坎普的试剂是为了获得2,3-环氧醇鉴于保持这些合成子的通用性进行在合成化学中用于通过合适的化学转化制备具有生物学重要性的各种分子。在该研究过程中，由于其温和的反应条件，Sharpsless不对称环氧化反应被发现是一种空前的替代方法，用于合成高度官能化的对映体纯的四氢呋喃衍生物。还研究了它们形成的详细机理。
• Synthesis of (−)-Deoxoprosophylline, (+)-2-<i>epi</i>-Deoxoprosopinine, and (2<i>R</i>,3<i>R</i>)- and (2<i>R</i>,3<i>S</i>)-3-Hydroxypipecolic Acids from <scp>d</scp>-Glycals
  作者：Hari Prasad Kokatla、Rima Lahiri、Pavan K. Kancharla、Venkata Ramana Doddi、Yashwant D. Vankar

  DOI：10.1021/jo100489k

  日期：2010.7.2

  New syntheses of (−)-deoxoprosophylline, (+)-2-epi-deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids are reported. Utilization of the chiral functionalities of Perlin aldehydes, derived from 3,4,6-tri-O-benzyl glycals, has been done along with chemoselective saturation of olefins and reductive aminations as key steps.

  报道了（-）-脱氧脯氨酸，（+）-2-表-脱氧胸苷，（2 R，3 R）-和（2 R，3 S）-3-羟基哌酸的新合成。衍生自3,4,6- tri - O-苄基缩醛的Perlin醛的手性官能团已被用作主要步骤，同时对烯烃进行了化学选择性饱和和还原性胺化反应。
• A consecutive approach towards the stereoselective synthesis of trisubstituted THF domains
  作者：Ram Sagar、L. Vijaya Raghava Reddy、Mohammad Saquib、Brijesh Kumar、Arun K. Shaw

  DOI：10.1016/j.tetasy.2006.12.010

  日期：2006.12

  A highly efficient, consecutive approach for the construction of synthetically valued, enantiomerically pure, trisubstituted THF domains 3-10 in a stereoselective manner starting from glycal derived allylic alcohols 1a-1d under Sharpless asymmetric epoxidation (SAE) conditions is reported. The reaction involves the intramolecular asymmetric ring opening (ARO) of in situ formed enantiopure 2,3-epoxy alcohols followed by protection of the diol. (c) 2006 Elsevier Ltd. All rights reserved.