3-((tert-butyldimethylsilyl)oxy)pentanedial | 459870-95-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-((tert-butyldimethylsilyl)oxy)pentanedial
• 英文别名: 3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]pentanedial；3-[tert-butyl(dimethyl)silyl]oxypentanedial
• CAS: 459870-95-2
• 化学式: C₁₁H₂₂O₃Si
• 分子量: 230.379
• InChiKey: WAQFCVMGCVWWEK-UHFFFAOYSA-N

物化性质

• 沸点：
  276.0±30.0 °C(Predicted)
• 密度：
  0.931±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((tert-butyldimethylsilyl)oxy)pentanedial 以 甲醇 为溶剂， 反应 66.0h， 生成 (3R)-(-)-methyl 3-<(tert-butyldimethylsilyl)oxy>-4-formylbutanoate
  参考文献：
  名称：

  去甲mevaldic酸替代物的非对映选择性和对映选择性制备通过去对称方法。（+）和（-）正甲戊内酯的对映选择性合成

  摘要：

  的无溶剂的去对称内消旋-dialdehyde与手性醇，导致制备的4-甲硅烷氧基-6- alkyloxytetrahydro -2- ħ -吡喃-2-酮用96％去衍生物。该方法可产生具有99％ee的相应甲基正甲羟戊酸酯，已应用于（-）-（R）和（+）-（S）甲羟戊酸内酯的对映选择性合成。

  DOI：

  10.1016/j.tet.2015.08.010
• 作为产物：
  描述：

  1,6-庚二烯-4-醇 在 咪唑 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 64.42h， 生成 3-((tert-butyldimethylsilyl)oxy)pentanedial
  参考文献：
  名称：

  nor-Mevaldic acid surrogates as selective antifungal agent leads against Botrytis cinerea. Enantioselective preparation of 4-hydroxy-6-(1-phenylethoxy)tetrahydro-2H-pyran-2-one

  摘要：

  Solvent-free desymmetrisation of meso-dialdehyde 1 with chiral 1-phenylethan-1-ol, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one (+)-3a with a 96: 4 dr Deprotected lactone (+)-19a and the related racemic lactones 16a-18a present a lactone moiety resembling the natural substrate of HMG-CoA reductase and their antifungal properties have been evaluated against the phytopathogenic fungi Botrytis cinerea and Colletotrichum gloeosporioides. These compounds were selectively active against B. cinerea, while inactive against C. gloeosporioides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.048

文献信息

• Total Synthesis of Dermostatin A
  作者：Yingchao Zhang、Carolynn C. Arpin、Aaron J. Cullen、Mark J. Mitton-Fry、Tarek Sammakia

  DOI：10.1021/jo2012658

  日期：2011.10.7

  The concise total synthesis of dermostatin A is described. Highlights include a two-directional application of the asymmetric acetate aldol method developed in our lab, a novel diastereotopic-group-selective acetal isomerization for terminus differentiation, and a selective cross-metathesis reaction between a terminal olefin and a trienal. A study of the scope and viability of similar cross-metathesis

  描述了dermostatin A的简明全合成。重点包括在我们实验室中开发的不对称乙酸羟醛方法的双向应用，用于末端区分的新型非对映异构基团选择性乙缩醛异构化以及末端烯烃与三烯醛之间的选择性交叉复分解反应。还描述了对类似的交叉易位反应的范围和生存能力的研究。合成是收敛的，并利用了大致相等复杂性的片段。
• The Total Synthesis of the Oxopolyene Macrolide RK-397
  作者：Mark J. Mitton-Fry、Aaron J. Cullen、Tarek Sammakia

  DOI：10.1002/anie.200602601

  日期：2007.2.5
• <i>N</i>-[6-(4-Butanoyl-5-methyl-1<i>H</i>-pyrazol-1-yl)pyridazin-3-yl]-5-chloro-1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1<i>H</i>-indole-3-carboxamide (SAR216471), a Novel Intravenous and Oral, Reversible, and Directly Acting P2Y12 Antagonist
  作者：Christophe Boldron、Angélina Besse、Marie-Françoise Bordes、Stéphanie Tissandié、Xavier Yvon、Benjamin Gau、Alain Badorc、Tristan Rousseaux、Guillaume Barré、Jérôme Meneyrol、Gernot Zech、Marc Nazare、Valérie Fossey、Anne-Marie Pflieger、Sandrine Bonnet-Lignon、Laurence Millet、Christophe Briot、Frédérique Dol、Jean-Pascal Hérault、Pierre Savi、Gilbert Lassalle、Nathalie Delesque、Jean-Marc Herbert、Françoise Bono

  DOI：10.1021/jm500588w

  日期：2014.9.11

  In the search of a potential backup for clopidogrel, we have initiated a HTS campaign designed to identify novel reversible P2Y12 antagonists. Starting from a hit with low micromolar binding activity, we report here the main steps of the optimization process leading to the identification of the preclinical candidate SAR216471. It is a potent, highly selective, and reversible P2Y12 receptor antagonist and by far the most potent inhibitor of ADP-induced platelet aggregation among the P2Y12 antagonists described in the literature. SAR216471 displays potent in vivo antiplatelet and antithrombotic activities and has the potential to differentiate from other antiplatelet agents.
• Desymmetrisation of dialdehydes: (+)-(S) and (−)-(R) nor-methyl mevaldate as versatile synthetic intermediates
  作者：Shirley L.J. Buckley、Michael G.B. Drew、Laurence M. Harwood、Antonio J. Macı́as-Sánchez

  DOI：10.1016/s0040-4039(02)00533-6

  日期：2002.5
• nor-Mevaldic acid surrogates as selective antifungal agent leads against Botrytis cinerea. Enantioselective preparation of 4-hydroxy-6-(1-phenylethoxy)tetrahydro-2H-pyran-2-one
  作者：José Manuel Botubol-Ares、María Jesús Durán-Peña、Rosario Hernández-Galán、Isidro G. Collado、Laurence M. Harwood、Antonio J. Macías-Sánchez

  DOI：10.1016/j.bmc.2015.04.048

  日期：2015.7

  Solvent-free desymmetrisation of meso-dialdehyde 1 with chiral 1-phenylethan-1-ol, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one (+)-3a with a 96: 4 dr Deprotected lactone (+)-19a and the related racemic lactones 16a-18a present a lactone moiety resembling the natural substrate of HMG-CoA reductase and their antifungal properties have been evaluated against the phytopathogenic fungi Botrytis cinerea and Colletotrichum gloeosporioides. These compounds were selectively active against B. cinerea, while inactive against C. gloeosporioides. (C) 2015 Elsevier Ltd. All rights reserved.