methyl (S)-3-tert-butyl-dimethylsilyloxy-4-oxo-butanoate | 289477-11-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (S)-3-tert-butyl-dimethylsilyloxy-4-oxo-butanoate
• 英文别名: methyl (3S)-3-[tert-butyl(dimethyl)silyl]oxy-4-oxobutanoate
• CAS: 289477-11-8
• 化学式: C₁₁H₂₂O₄Si
• 分子量: 246.379
• InChiKey: VYZWLLYPOUFHJP-VIFPVBQESA-N

物化性质

• 沸点：
  251.5±30.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  16
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (S)-3-tert-butyl-dimethylsilyloxy-4-oxo-butanoate 在 4-甲基苯磺酸吡啶 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (4S,5R)-4-(tert-butyldimethylsilyloxy)-5-phenylpyrrolidin-2-one
  参考文献：
  名称：

  Diastereoconvergent Synthesis of trans-5-Hydroxy-6-Substituted-2-Piperidinones by Addition–Cyclization–Deprotection Process

  摘要：

  A diastereoselective one-pot approach to access trans-5-hydroxy-6-substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by alpha-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.

  DOI：

  10.1021/ol5020812
• 作为产物：
  描述：

  L-苹果酸二甲酯 在 sodium tetrahydroborate 、 dimethyl sulfide borane 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl (S)-3-tert-butyl-dimethylsilyloxy-4-oxo-butanoate
  参考文献：
  名称：

  A Configurationally Stable Alkoxy Allenyl Zinc Reagent, en Route to anti-anti Vicinal Amino Diols

  摘要：

  [GRAPHICS]The reaction of an alkoxyallenyl zinc reagent with benzyl imines derived from lactic and mandelic acids proceeds highly diastereoselectively and leads to 2-amino-1,3-diol derivatives with an anti-anti pattern.

  DOI：

  10.1021/ol015941a

文献信息

• Highly stereoselective synthesis of enantiomerically pure β-hydroxy-γ-sulfenyl-γ-butyrolactone by asymmetric Pummerer type cyclization
  作者：Guy Solladié、Nicole Wilb、Claude Bauder

  DOI：10.1016/s0040-4039(00)00562-1

  日期：2000.5

  Enantiomerically pure t-butyl 4-sulfinyl-3-silyloxy-butanoate can be transformed stereoselectively in a Pummerer reaction with TFAA into the usual aldehyde or into a cis β-hydroxy-γ-sulfenyl-γ-butyrolactone. Experimental conditions allowing total control of the reaction in favor of either the aldehyde or the γ-butyrolactone are described. The corresponding methyl butanoate led, under the same conditions

  对映体纯的4-亚磺酰基-3-甲硅烷基氧基-丁酸叔丁基酯可以在与TFAA的Pummerer反应中立体选择性地转化为通常的醛或顺式β-羟基-γ-亚磺酰基-γ-丁内酯。描述了允许完全控制反应以利于醛或γ-丁内酯的实验条件。在相同条件下，相应的丁酸甲酯仅导致醛。
• WO2007/17117
  申请人：——

  公开号：——

  公开（公告）日：——
• Diastereoconvergent Synthesis of <i>trans</i>-5-Hydroxy-6-Substituted-2-Piperidinones by Addition–Cyclization–Deprotection Process
  作者：Chang-Mei Si、Wei Huang、Zhen-Ting Du、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1021/ol5020812

  日期：2014.8.15

  A diastereoselective one-pot approach to access trans-5-hydroxy-6-substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by alpha-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.
• A Configurationally Stable Alkoxy Allenyl Zinc Reagent, en Route to <i>a</i><i>nti</i>-<i>a</i><i>nti</i> Vicinal Amino Diols
  作者：Jean-François Poisson、Jean F. Normant

  DOI：10.1021/ol015941a

  日期：2001.6.1

  [GRAPHICS]The reaction of an alkoxyallenyl zinc reagent with benzyl imines derived from lactic and mandelic acids proceeds highly diastereoselectively and leads to 2-amino-1,3-diol derivatives with an anti-anti pattern.