(S)-1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-ol | 885674-86-2

• 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: (S)-1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-ol
• 英文别名: (3S)-1-[(4-methoxyphenyl)methoxy]-2,2-dimethylhex-5-en-3-ol
• CAS: 885674-86-2
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: PCTDCBULSRSDRG-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-ol 在 2,6-二甲基吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 aq. phosphate buffer 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 (S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethylhex-5-en-1-ol
  参考文献：
  名称：

  Studies on C18-C20 Aldol Couplings of Rhizopodin

  摘要：

  The aldol addition of an enol(ate) to a carbonyl compound is one of the most powerful and versatile C-C bond forming reactions. In complex target synthesis the coupling of two chiral partners may complicate the stereochemical outcome by multiple stereoinductions. Here, we report studies on pivotal aldol couplings employed in the rhizopodin synthesis, detailing the various directing effects exerted by the stereogenic centers present in this sterically hindered connection.

  DOI：

  10.1055/s-0033-1338493
• 作为产物：
  描述：

  D-(-)-泛酰内酯 在 盐酸 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 sodium hydride 、 对甲苯磺酸 、 1-对甲基苯磺酰咪唑 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 33.5h， 生成 (S)-1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-ol
  参考文献：
  名称：

  Bryostatins: The asymmetric synthesis of C1-C9 and C11-C16 fragments

  摘要：

  The fragments C1-C-9 19 and C-11-C-16 26 of the bryostatins are constructed in an enantioselective and highly diastereoselective fashion from respectively D-pantolactone (2) and L-erythrulose (3) as chiral templates.

  DOI：

  10.1016/0040-4039(91)85096-n

文献信息

• Bryostatins: The Asymmetric Synthesis of the C₁-C₉and C₁₇-C₂₇Fragments
  作者：Jef De Brabander、Maurits Vandewalle

  DOI：10.1055/s-1994-25589

  日期：——

  The construction of the fragments C1-C9 3 and C17-C27, 4a of the bryostatins in a enantioselective and highly diastereoselective fashion is described. The usefulness of the "chiron" approach is illustrated with the synthesis of these fragments from, respectively, D-pantolactone (6) and D-isobutyl lactate (23) as chiral templates.

  构建了布雷抑酶素（bryostatins）的片段C1-C9 3和C17-C27 4a，采用了对映选择性和高非对映选择性的方式。通过分别以D-泛醇内酯（6）和D-异丁基乳酸酯（23）为手性模板合成这些片段，说明了“四手型”方法的实用性。
• Modular Total Synthesis of Rhizopodin: A Highly Potent G-Actin Dimerizing Macrolide
  作者：Manuel Kretschmer、Michael Dieckmann、Pengfei Li、Sven Rudolph、Daniel Herkommer、Johannes Troendlin、Dirk Menche

  DOI：10.1002/chem.201302197

  日期：2013.11.18

  A highly convergent total synthesis of the potent polyketide macrolide rhizopodin has been achieved in 29 steps by employing a concise strategy that exploits the molecule′s C2 symmetry. Notable features of this convergent approach include a rapid assembly of the macrocycle through a site‐directed sequential cross‐coupling strategy and the bidirectional attachment of the side chains by means of Hor

  通过采用利用分子的C 2对称性的简洁策略，已在29个步骤中实现了强聚合的大酮化合物大环内酯大根内酯的高度收敛的全合成。这种收敛方法的显着特点包括通过定点顺序交叉偶联策略快速组装大环，以及通过Horner-Wadsworth-Emmons（HWE）偶联反应实现侧链的双向连接。在此过程中，开发了可扩展的路线，用于合成三个复杂程度相近的主要构件，从而实现了其立体控制构造。该模块化途径将适合于根瘤菌素其他类似物的合成的开发。
• Concise Synthesis of the Macrocyclic Core of Rhizopodin by a Heck Macrocyclization Strategy
  作者：Michael Dieckmann、Sven Rudolph、Sandra Dreisigacker、Dirk Menche

  DOI：10.1021/jo302134y

  日期：2012.12.7

  A highly convergent synthesis of the central dimeric core of the potent antibiotic macrolide rhizopodin is reported. Notable features of the highly concise route include an effective preparation of the key C8-C22 building block based on an iridium-catalyzed Krische allylation and a chemoselective cross-coupling approach toward the macrocycle involving a highly advantageous Heck reaction for macrocyclization

  据报道，强效抗生素大环内酯类根瘤菌素的中央二聚体核心的高度收敛合成。高度简洁的路线的显着特征包括基于铱催化的Krische烯丙基化有效制备关键的C8-C22构建基团，以及对大环化合物进行化学选择性交叉偶联的方法，其中涉及用于大环化的高度有利的Heck反应。
• Synthesis of a Tetradehydro-Disorazole C1
  作者：Barbara Niess、Ingo V. Hartung、Lars O. Haustedt、H. Martin R. Hoffmann

  DOI：10.1002/ejoc.200500675

  日期：2006.3

  The synthesis of a protected 9,9′,10,10′-tetradehydro-disorazole C1 is described. A C1–C8 oxazole fragment with an E-vinylic iodide terminus is coupled to a suitable C9–C19 enyne. The resulting ω-hydroxycarboxylic acid is cyclodimerized stepwise via intermolecular esterification, followed by lactonization. In addition, simplified masked analogues of disorazole C1 with truncated side chains are prepared

  描述了受保护的 9,9',10,10'-四脱氢-二恶唑 C1 的合成。带有 E-乙烯基碘化物末端的 C1-C8 恶唑片段与合适的 C9-C19 烯炔偶联。所得ω-羟基羧酸通过分子间酯化逐步环二聚，然后内酯化。此外，还制备了具有截短侧链的 disorazole C1 的简化掩蔽类似物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Stereoselective Synthesis of 1,3-<i>anti</i> Diols by an Ipc-Mediated Domino Aldol-Coupling/Reduction Sequence
  作者：Michael Dieckmann、Dirk Menche

  DOI：10.1021/ol3033303

  日期：2013.1.4

  A novel domino process for 1,3-anti diol synthesis by the union of a methyl ketone with an aldehyde is described. The operationally simple procedure is based on an Ipc-boron-aldol coupling and subsequent Ipc-mediated reduction of the intermediate beta-hydroxy-ketone. The sequence proceeds with excellent anti-selectivities and enables the rapid construction of complex polyketide fragments.