(2R,3S)-2-Benzyloxy-hex-5-en-3-ol | 89104-02-9

• 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: (2R,3S)-2-Benzyloxy-hex-5-en-3-ol
• 英文别名: (2R,3S)-2-phenylmethoxyhex-5-en-3-ol
• CAS: 89104-02-9
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: WHJDLQGVVYDCOC-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-Benzyloxy-hex-5-en-3-ol 在 氨基磺酰氯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 以79%的产率得到(±)-(2R,3S)-2-(benzyloxy)hex-5-en-3-yl sulfamate
  参考文献：
  名称：

  金（I）催化束缚在烯丙醇上的氨基磺酸酯的分子内脱水胺化：环状环氨基磺酸盐的合成策略

  摘要：

  通过束缚在烯丙醇上的氨基磺酸酯的催化分子内环化作用，已经开发了环状氨基磺酸酯的有效合成方案。反应在室温下在（IPr）AuCl（5 mol％）和AgBF 4（5 mol％）的存在下顺利进行。该方案的特点是产率高，选择性好，选择性高，底物范围广和反应条件温和。该方法也适用于七元氨基磺酸盐的合成。

  DOI：

  10.1002/adsc.202001330
• 作为产物：
  描述：

  (R)-2-苄氧基-1-丙醇 在 草酰氯 、 二甲基砜 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2R,3S)-2-Benzyloxy-hex-5-en-3-ol
  参考文献：
  名称：

  Stereoselective synthesis of C19–C27 fragment of bryostatin 11

  摘要：

  A convergent synthesis of C19-C27 fragment (2) of bryostatin-11 is described. The key steps involved in this approach are kinetic resolution, Grignard reaction, and Sharpless dihydroxylation. AIBN catalyzed radical cyclization strategy has been used for the first time to construct the six-membered pyran system. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.05.116

文献信息

• Stereoselective addition of organomanganese reagents to chiral acylsilanes and aldehydes
  作者：Céline Boucley、Gérard Cahiez、Silvia Carini、Vanda Cerè、Mauro Comes-Franchini、Paul Knochel、Salvatore Pollicino、Alfredo Ricci

  DOI：10.1016/s0022-328x(00)00902-5

  日期：2001.4

  Organomanganese halides and organomanganates prepared by transmetalation of organolithium and Grignard reagents add smoothly to the carbonyl moiety of acylsilanes and of substituted aldehydes bearing a chiral center at the α-position affording the desired alcohols in good to excellent yields and with essentially no undesired products from enolization. Comparison of the stereochemical outcome with that

  通过有机锂和格氏试剂的金属转移而制备的有机锰卤化物和有机锰酸盐可平滑地添加到酰基硅烷和取代醛的羰基部分上，该醛在α-位带有手性中心，可提供所需醇，收率良好至极佳，并且基本上没有烯醇化产生的不良产物。将立体化学结果与其他有机金属物种所观察到的结果进行了比较，概述了有机锰试剂诱导均一的良好非对映选择性的能力，在许多情况下，其显着高于先前对这些反应的报道。在酰基硅烷12的比较中清楚地显示了R 3 Si基团在促进高1,2-不对称感应中所发挥的关键作用。与相应的醛13。Cram /抗Cram选择性的含义取决于参与这些反应的羰基试剂的性质。
• Synthetic Approaches to the Bottom Half Fragment for Bryostatin 11
  作者：Kyoko Nakagawa-Goto、Michael Crimmins

  DOI：10.1055/s-0030-1260784

  日期：2011.7

  An approach towards the stereoselective synthesis of the bottom half fragment of bryostatin 11 is described. Key steps include asymmetric aldol and Saksena-Evans reduction reactions to construct multiple stereogenic centers and thioketalization-lactonization reactions to form the thioketal-protected C-ring.

  描述了一种立体选择性合成苔藓抑素 11 下半片段的方法。关键步骤包括不对称醛醇和 Saksena-Evans 还原反应以构建多个立体中心和硫缩酮化-内酯化反应以形成硫缩酮保护的 C 环。
• Synthesis and pharmacological investigation of the enantiomers of muscarone and allo-muscarone
  作者：Marco De Amici、Clelia Dallanoce、Carlo De Micheli、Enzo Grana、Annalisa Barbieri、Herbert Ladinsky、GiovanniBattista Schiavi、Franco Zonta

  DOI：10.1021/jm00088a029

  日期：1992.5

  functional tests, (-)-1 (2S,5S) and (-)-5 (2R,5S) were the eutomers of muscarone and allomuscarone, respectively. The eudismic ratio of muscarone, evaluated in the functional tests, spanned a range of 280-440. These values are substantially different from ones (2.4-10.1) reported in the literature. From a stereochemical point of view, muscarone behaves as muscarine and all other major muscarinic agonists; as

  基于使用（R）-和（S）-乳酸酯作为起始原料的策略，可以合成穆斯卡隆[（-）-1和（+）-1]和别甲香酮[（-）- 5和（+）-5]的对映体过量大于98％。检查了化合物与大脑皮层（M1），心脏（M2）和唾液腺（M3）的膜结合以及识别毒蕈碱受体亲和激动剂状态的能力。还通过五种功能测定法测试了两对对映异构体，并确定了它们的毒蕈碱效力。在结合力和功能测试中，（-）-1（2S，5S）和（-）-5（2R，5S）分别是穆斯卡隆和异源香豆素的体。在功能测试中评估的穆斯卡隆的普遍比例在280-440之间。这些值与（2.4-10。1）文献报道。从立体化学的观点来看，穆斯卡隆的行为与穆斯卡因和所有其他主要的毒蕈碱激动剂相同。结果，解释穆斯卡隆异常的假说不再存在。
• Acyclic stereoselection. 20. High diastereofacial selectivity in the stannic chloride mediated reactions of allylsilanes with chiral α- and β-alkoxy aldehydes.
  作者：Syun-ichi Kiyooka、Clayton H Heathcock

  DOI：10.1016/s0040-4039(00)94002-4

  日期：1983.1

  Stannic chloride is an effective catalyst for the reaction of allylsilanes with chiral α- and β-alkoxy aldehydes. In the case of α-alkoxy aldehyde 1, the diastereofacial preference is outstanding (>35:1). With β- alkoxy aldehydes 5 and 6, selectivity is lower, but still quite acceptable (7–12:1).

  氯化锡是烯丙基硅烷与手性α-和β-烷氧基醛反应的有效催化剂。在α-烷氧基醛1的情况下，非对面优先性是突出的（> 35：1）。使用β-烷氧基醛5和6时，选择性较低，但仍然可以接受（7–12：1）。
• Comparative Diastereoselectivity Analysis of Crotylindium and 3-Bromoallylindium Additions to α-Oxy Aldehydes in Aqueous and Nonaqueous Solvent Systems
  作者：Leo A. Paquette、Thomas M. Mitzel

  DOI：10.1021/jo9613489

  日期：1996.1.1

  The couplings of crotyl bromide (1) and 1,3-dibromopropene (2) to a triad of conformationally unrestricted a-oxy aldehydes in water, aqueous THF (1:1), and anhydrous THF are described. In no example involving 1 was the formation of anti,syn product detected. The proportion of syn isomers reached a maximum (syn/anti = 5.6:1) when the neighboring hydroxyl group was unprotected and water was the reaction medium. Although internal chelation also operates to some degree with 2, considerable erosion of this mechanistic pathway (maximum now only 2:1) in favor of Felkin and ''anti-Felkin'' transition states is reflected in the product distributions. This trend can be synthetically advantageous, and a utilitarian example is demonstrated. The indium reagents studied here are notably efficient nucleophilic reaction partners in water.