di-tert-butyl (2R,3S)-4-<(R)-1-hydroxy-1-phenylmethyl>-1,4-dioxaspiro<4.4>nonane-2,3-dicarboxylate | 193957-60-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: di-tert-butyl (2R,3S)-4-<(R)-1-hydroxy-1-phenylmethyl>-1,4-dioxaspiro<4.4>nonane-2,3-dicarboxylate
• 英文别名: ditert-butyl (2S,3R)-3-[(R)-hydroxy(phenyl)methyl]-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylate
• CAS: 193957-60-7
• 化学式: C₂₄H₃₄O₇
• 分子量: 434.53
• InChiKey: DKMXRYOESKPYSW-QZTZHPFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (2R,3S)-4-<(R)-1-hydroxy-1-phenylmethyl>-1,4-dioxaspiro<4.4>nonane-2,3-dicarboxylate 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 反应 46.0h， 以57%的产率得到(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 、 Ti(OiPr)Cl3 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， -78.0~60.0 ℃ 、26.66 kPa 条件下， 反应 7.5h， 生成 di-tert-butyl (2R,3S)-4-<(R)-1-hydroxy-1-phenylmethyl>-1,4-dioxaspiro<4.4>nonane-2,3-dicarboxylate
  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：——
• Aldol reactions of ketal-protected tartrate ester enolates. Asymmetric syntheses and absolute stereochemical assignments of phospholipase A2 inhibitors cinatrin C1 and C3
  作者：David A. Evans、B. Wesley Trotter、James C. Barrow

  DOI：10.1016/s0040-4020(97)90390-2

  日期：1997.6

  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.