[(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methanol | 740845-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: [(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methanol
• 英文别名: [(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methanol
• CAS: 740845-32-3
• 化学式: C₁₂H₂₆O₃Si
• 分子量: 246.422
• InChiKey: NERBBRIJPYIFSZ-GHMZBOCLSA-N

物化性质

• 沸点：
  289.2±25.0 °C(predicted)
• 密度：
  0.96±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  [(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methanol 在 ruthenium trichloride 、 sodium periodate 、 正丁基锂 、 草酰氯 、 二甲基亚砜 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.25h， 生成 2-[(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]acetic acid
  参考文献：
  名称：

  新型大环内酯类化合物的合成及阳离子络合性质

  摘要：

  据报道，顺式-2-烷基-3-氧基-四氢吡喃单元是一种新型结构，用于设计和合成具有C 2对称性的新型离子载体。研究了七个不同的大环内酯和冠醚的合成及其阳离子络合性能。一些受体的X射线晶体结构提供了关于固态四氢吡喃的优选构象的有价值的信息，该构象可能与溶液中的阳离子络合特性有关。动力学模板效应已被证明是在大环氧化物3合成中提高产率和选择性的有用工具。

  DOI：

  10.1016/j.tet.2005.06.034
• 作为产物：
  描述：

  D-三乙酰半乳糖烯 在 咪唑 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 [(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methanol
  参考文献：
  名称：

  Synthesis and antiproliferative activity of (2R,3R)-disubstituted tetrahydropyrans

  摘要：

  In this study, we synthesized a series of enantiomerically pure (2R,3R)-disubstituted tetrahydropyrans with diverse functional groups. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780 (ovarian cancer), SW1573 (non-small cell lung cancer), and WiDr (colon cancer). Overall, the results show the relevance for antiproliferative activity of the alpha,beta-unsaturated ester side chain at position 2 of the THP ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.094

文献信息

• Synthesis and cation complexation properties of new macrolides
  作者：Romen Carrillo、Victor S. Martín、Matías López、Tomás Martín

  DOI：10.1016/j.tet.2005.06.034

  日期：2005.8

  design and synthesis of a new type of ionophores with C2-symmetry is reported. The synthesis of seven different macrolides and a crown ether and their cation complexation properties were investigated. The X-ray crystal structure of some of the receptors provides valuable information on the preferred conformation of tetrahydropyrans in the solid state that can be related to the cation complexation properties

  据报道，顺式-2-烷基-3-氧基-四氢吡喃单元是一种新型结构，用于设计和合成具有C 2对称性的新型离子载体。研究了七个不同的大环内酯和冠醚的合成及其阳离子络合性能。一些受体的X射线晶体结构提供了关于固态四氢吡喃的优选构象的有价值的信息，该构象可能与溶液中的阳离子络合特性有关。动力学模板效应已被证明是在大环氧化物3合成中提高产率和选择性的有用工具。
• Tetrahydropyran-Based Hybrid Dipeptides as Asymmetric Catalysts for Michael Addition of Aldehydes to β-Nitrostyrenes
  作者：Jorge Borges-González、Andrés Feher-Voelger、Fernando Pinacho Crisóstomo、Ezequiel Q. Morales、Tomás Martín

  DOI：10.1002/adsc.201601193

  日期：2017.2.20

  A new series of hybrid dipeptide‐like organocatalysts based on pyranoid ϵ‐ or ζ‐amino acids and proline have been prepared for the asymmetric Michael addition of aldehydes to β‐nitrostyrenes. The reaction proceeds under mild conditions to afford a wide range of γ‐nitroaldehydes with up to 98% yield and up to 96% ee. These dipeptides are bifunctional organocatalysts, with a proline at the N‐terminus

  已经制备了一系列新的基于吡喃型ϵ-或ζ-氨基酸和脯氨酸的杂二肽样有机催化剂，用于将醛不对称地迈克尔加成至β-硝基苯乙烯。反应在温和的条件下进行，以提供高达98％的收率和96％ee的多种γ-硝基醛。这些二肽是双功能有机催化剂，在N端带有脯氨酸，在C端带有羧酸。嵌入ϵ-或ζ-氨基酸的四氢吡喃单元可诱导明确定义的构象，该构象负责催化作用。这些二肽代表一种新型的有机催化剂，具有调节其反应性和选择性的大量可能性。
• The cis-2-alkyl-3-oxy-tetrahydropyran unit as a building block for new ionophores with C2-symmetry
  作者：Romen Carrillo、Victor S. Martı́n、Tomás Martı́n

  DOI：10.1016/j.tetlet.2004.05.036

  日期：2004.6

  The use of cis-2-alkyl-3-oxy-tetrahydropyran unit is reported as a novel structure for the design and synthesis of a new type of ionophore with C-2-symmetry. The synthesis of five macrolides and their complexation properties were investigated. The template effect as an effective tool to improve the selectivity and yield in the macrolactonization process is described. (C) 2004 Elsevier Ltd. All rights reserved.
• Correlation between Conformational Equilibria of Free Host and Guest Binding Affinity in Non-preorganized Receptors
  作者：Romen Carrillo、Ezequiel Q. Morales、Víctor S. Martín、Tomás Martín

  DOI：10.1021/jo400683j

  日期：2013.8.16

  Positive cooperativity between host conformational equilibria and guest binding has been widely reported in protein receptors. However, reported examples of this kind of cooperativity in synthetic hosts are scarce and largely serendipitous, among other things because it is hard to envision systems which display this kind of cooperativity. In order to shed some light on the correlation between conformational equilibria of free host and guest binding, selected structural modifications have been performed over a family of nonpreorganized hosts in order to induce conformational changes and to analyze their effect on the binding affinity. The conformational effect was evaluated by a theoretical conformational search and correlated with the ability of the receptors. All data suggest that those receptors that display the best association constants are able to sample folded conformations analogous to the conformational requirements for the binding of the guests. On the contrary, for those receptors where folded conformers are scarce, then the association constant and enantioselectivity clearly drop.
• Synthesis and antiproliferative activity of (2R,3R)-disubstituted tetrahydropyrans. Part 2: Effect of side chain homologation
  作者：Romen Carrillo、Leticia G. León、Tomás Martı´n、Vı´ctor S. Martı´n、José M. Padrón

  DOI：10.1016/j.bmcl.2006.10.066

  日期：2007.2

  In this study, we synthesized a series of enantiomerically pure (2R,3R)- and (2R, 3 S)-disubstituted tetrahydropyrans bearing a CH2O spacer group on the side chain at position 2 of the heterocyclic ring. The in vitro antiproliferative activities of the compounds were examined in the human solid tumor cell lines A2780 (ovarian cancer), SW1573 (non-small cell lung cancer), and WiDr (colon cancer). Overall, the results point out the relevance for anti proliferative activity of the distance between the heterocycle and the unsaturated group. (c) 2006 Elsevier Ltd. All rights reserved.