2-{[(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}acetic acid | 740845-35-6

• 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: 2-{[(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}acetic acid
• 英文别名: 2-[[(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methoxy]acetic acid
• CAS: 740845-35-6
• 化学式: C₁₄H₂₈O₅Si
• 分子量: 304.459
• InChiKey: YZMHSHIQHKGJPD-VXGBXAGGSA-N

物化性质

• 沸点：
  390.3±37.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-{[(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}acetic acid 在 palladium dihydroxide 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 氢氟酸 、 氢气 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 14.0h， 生成 [(2R,3R)-2-[(2-oxo-2-pyridin-2-ylsulfanylethoxy)methyl]oxan-3-yl] 2-[[(2R,3R)-3-hydroxyoxan-2-yl]methoxy]acetate
  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：

  叔丁基二甲基氯硅烷 在 咪唑 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 2-{[(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}acetic acid
  参考文献：
  名称：

  Synthesis and antiproliferative activity of (2R,3R)-disubstituted tetrahydropyrans. Part 2: Effect of side chain homologation

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2006.10.066

文献信息

• 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.
• 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。
• 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.