tert-butyl-(2S,3S)-1,4-dioxaspiro[4.4]nonane-3-(1-tert-butoxy-1-trimethylsilyloxymethylenyl)-2-carboxylate | 193957-62-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl-(2S,3S)-1,4-dioxaspiro[4.4]nonane-3-(1-tert-butoxy-1-trimethylsilyloxymethylenyl)-2-carboxylate
• CAS: 193957-62-9
• 化学式: C₂₀H₃₆O₆Si
• 分子量: 400.588
• InChiKey: GJUGHFQLGAFBSH-AWEZNQCLSA-N

物化性质

• 沸点：
  412.5±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl-(2S,3S)-1,4-dioxaspiro[4.4]nonane-3-(1-tert-butoxy-1-trimethylsilyloxymethylenyl)-2-carboxylate 在 Ti(OiPr)Cl3 、 camphor-10-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 47.0h， 生成 (3S,4R,5R)-4-carboxy-3,4-dihydroxytetrahydro-2-oxo-5-phenylfuran, tert-butyl ester
  参考文献：
  名称：

  Aldol reactions of ketal-protected tartrate ester enolates. Asymmetric syntheses and absolute stereochemical assignments of phospholipase A2 inhibitors cinatrin C1 and C3

  摘要：

  An efficient approach to the syntheses of cinatrins C-1 and C-3 has been developed and used to establish the absolute configurations of these natural products. The construction of each molecule has been achieved in a five-step reaction sequence (overall yield 43% for cinatrin C-1, 33% for cinatrin C-3) from the di-tert-butyl ester of (R,R)-tartaric acid. The two contiguous, quaternary chiral centers in the cinatrin skeleton are constructed via a diastereoselective, titanium-mediated aldol coupling of a tartrate-derived silylketene acetal and an achiral alpha-ketoester. This bond construction proceeds with excellent diastereoselectivity for a variety of aldehyde and alpha-ketoester substrates. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)90390-2
• 作为产物：
  描述：

  1,1-二甲氧基环戊烷 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， -78.0~60.0 ℃ 、26.66 kPa 条件下， 反应 6.5h， 生成 tert-butyl-(2S,3S)-1,4-dioxaspiro[4.4]nonane-3-(1-tert-butoxy-1-trimethylsilyloxymethylenyl)-2-carboxylate
  参考文献：
  名称：

  Aldol reactions of ketal-protected tartrate ester enolates. Asymmetric syntheses and absolute stereochemical assignments of phospholipase A2 inhibitors cinatrin C1 and C3

  摘要：

  An efficient approach to the syntheses of cinatrins C-1 and C-3 has been developed and used to establish the absolute configurations of these natural products. The construction of each molecule has been achieved in a five-step reaction sequence (overall yield 43% for cinatrin C-1, 33% for cinatrin C-3) from the di-tert-butyl ester of (R,R)-tartaric acid. The two contiguous, quaternary chiral centers in the cinatrin skeleton are constructed via a diastereoselective, titanium-mediated aldol coupling of a tartrate-derived silylketene acetal and an achiral alpha-ketoester. This bond construction proceeds with excellent diastereoselectivity for a variety of aldehyde and alpha-ketoester substrates. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)90390-2

文献信息

• Agganval, Varinder K.; Masters, Susannah J.; Adams, Harry, Journal of the Chemical Society. Perkin transactions I, 1999, # 2, p. 155 - 162
  作者：Agganval, Varinder K.、Masters, Susannah J.、Adams, Harry、Spey, Sharon E.、Brown, George R.、Foubister, Alan J.

  DOI：——

  日期：——