tert-butyldimethylsilyl (R)-2-((tert-butyldimethylsilyl)oxy)-2-phenylacetate | 140840-38-6

• 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: tert-butyldimethylsilyl (R)-2-((tert-butyldimethylsilyl)oxy)-2-phenylacetate
• CAS: 140840-38-6
• 化学式: C₂₀H₃₆O₃Si₂
• 分子量: 380.675
• InChiKey: FNVJWYFVHSEHFW-QGZVFWFLSA-N

物化性质

• 沸点：
  379.2±35.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl (R)-2-((tert-butyldimethylsilyl)oxy)-2-phenylacetate 在 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(tert-butyldimethylsilyloxy)phenylacetyl chloride
  参考文献：
  名称：

  对映体纯的实际合成肌醇肌醇衍生物

  摘要：

  对映体纯的肌醇衍生物的合成是使用扁桃酸衍生的酰基保护基完成的。

  DOI：

  10.1016/s0040-4039(00)91846-x
• 作为产物：
  描述：

  benzyl (R)-(2-hydroxy-2-phenylacetoxy)carbamate 在 咪唑 、 Enterobacter cloacae P99 β-lactamase 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyldimethylsilyl (R)-2-((tert-butyldimethylsilyl)oxy)-2-phenylacetate
  参考文献：
  名称：

  Serendipitous Discovery of α-Hydroxyalkyl Esters as β-Lactamase Substrates

  摘要：

  O-(1-Carboxy-1-alkyloxycarbonyl) hydroxamates were found to spontaneously decarboxylate in aqueous neutral buffer to form O-(2-hydroxyalkylcarbonyl) hydroxamates, While the former molecules do not react rapidly with serine beta-lactamases, the latter are quite good substrates of representative class A and C, but not D, enzymes, and particularly of a class C enzyme. The enzymes catalyze hydrolysis of these compounds to a mixture of the alpha-hydroxy acid and hydroxamate. Analogous compounds containing aryloxy leaving groups rather that hydroxamates are also substrates. Structure-activity experiments showed that the alpha-hydroxyl group was required for any substantial substrate activity. Although both D- and L-alpha-hydroxy acid derivatives were substrates, the former were preferred. The response of the class C activity to pH and to alternative nucleophiles (methanol and D-phenylalanine) suggested that the same active site functional groups participated in catalysis as for classical substrates. Molecular modeling was employed to explore how the alpha-hydroxy group might interact with the class C beta-lactamase active site. Incorporation of the alpha-hydroxyalkyl moiety into novel inhibitors will be of considerable interest.

  DOI：

  10.1021/bi101071r

文献信息

• A Chiral Pool Strategy for the Synthesis of Enantiopure Hydroxymethyl-Substituted Pyridine Derivatives
  作者：Christian Eidamshaus、Hans-Ulrich Reissig

  DOI：10.1002/ejoc.201100681

  日期：2011.10

  A simple procedure for the synthesis of enantiopure hydroxymethyl-substituted pyridine derivatives is presented. The developed method is based on TMSOTf-promoted cyclocondensations of β-ketoenamides, leading to differently substituted 4-hydroxypyridine/4-pyridone derivatives. The required β-ketoenamides were prepared by acylation ofeasily available enamino ketones with suitably protected enantiopure

  介绍了合成对映体纯羟甲基取代吡啶衍生物的简单程序。开发的方法基于 TMSOTf 促进的 β-酮烯酰胺环缩合反应，导致不同取代的 4-羟基吡啶/4-吡啶酮衍生物。所需的 β-酮烯酰胺是通过将容易获得的烯氨基酮与适当保护的对映体纯羧酰氯酰化来制备的。大多数实验是用 D-扁桃酸作为起始材料进行的。已经表明所有步骤基本上没有外消旋化。几种制备的 4-吡啶酮衍生物转化为相应的 pyrid-4-yl nonaflates 并进行一系列钯催化的转化，如 Suzuki、Heck 或 Sonogashira 反应。此外，不对称 2,6-二取代吡啶衍生物的区域选择性侧链官能化是通过应用相应吡啶 N-氧化物的 Boekelheide 重排来实现的。所提出的方法为高度取代的对映纯吡啶衍生物提供了一种灵活、快速和可扩展的方法。
• Accessing Diverse Cross-Benzoin and α-Siloxy Ketone Products via Acyl Substitution Chemistry
  作者：Chloe N. Larcombe、Lara R. Malins

  DOI：10.1021/acs.joc.2c00801

  日期：2022.7.15

  An approach to diverse cross-benzoin and α-siloxy ketone products which leverages a simple yet underutilized C–C bond disconnection strategy is reported. Acyl substitution of readily accessible α-siloxy Weinreb amides with organolithium compounds enables access to a broad scope of aryl, heteroaryl, alkyl, alkenyl, and alkynyl derivatives. Enantiopure benzoins can be accessed via a chiral pool approach

  报道了一种利用简单但未充分利用的 C-C 键断开策略的多种交叉苯偶姻和 α-甲硅烷氧基酮产品的方法。用有机锂化合物对容易获得的 α-甲硅烷氧基 Weinreb 酰胺进行酰基取代，可以获得广泛的芳基、杂芳基、烷基、烯基和炔基衍生物。对映体纯苯偶姻可以通过手性池方法获得，并且在一系列下游合成应用中突出了可访问的交叉苯偶姻和 α-甲硅烷氧基酮的效用。