di-tert-butyl (2S,3S)-1,4-dioxaspiro<4.4>nonane-2,3-dicarboxylate | 164217-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: di-tert-butyl (2S,3S)-1,4-dioxaspiro<4.4>nonane-2,3-dicarboxylate
• 英文别名: di-tert-butyl-(2S,3S)-1,4-dioxaspiro<4.4>nonane-2,3-carboxylate；ditert-butyl (2S,3S)-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylate
• CAS: 164217-15-6
• 化学式: C₁₇H₂₈O₆
• 分子量: 328.406
• InChiKey: UDXZSVTXFJBQFH-RYUDHWBXSA-N

物化性质

• 沸点：
  387.3±37.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (2S,3S)-1,4-dioxaspiro<4.4>nonane-2,3-dicarboxylate 在 正丁基锂 、 Ti(OiPr)Cl3 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 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
• 作为产物：
  描述：

  (2S,3S)-2,3-Bis-(2-chloro-acetoxy)-succinic acid di-tert-butyl ester 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 苯 为溶剂， 60.0 ℃ 、26.66 kPa 条件下， 反应 6.28h， 生成 di-tert-butyl (2S,3S)-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

• Asymmetric Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C
  作者：David A. Evans、James C. Barrow、James L. Leighton、Albert J. Robichaud、Michael Sefkow

  DOI：10.1021/ja00105a085

  日期：1994.12

  Merck2 and Glaxo,' a number of closely related structures sharing the common 2,8-dioxabicyclo[3.2. lloctane core have been isolated and characterized to date. The purpose of this communication is to disclose a route to the synthesis of zaragozic acid C (1)5 which is amenable to the synthesis of the other members of this family of natural products.6

  最近发现的被称为角鲨烯酸和萨拉戈齐酸 2 的真菌代谢物已成为合成的有吸引力的目标，因为它们对角鲨烯合酶 (EC 2.5.1.21) 有皮摩尔抑制作用，这是甾醇生物合成中的第一个关键步骤。还发现该天然产物家族的成员是法马磺酰蛋白转移酶的有效抑制剂。在默克 2 和葛兰素史克的独立研究中，许多密切相关的结构共享共同的 2,8-二氧杂双环 [3.2]。迄今为止，lloctane 核已被分离和表征。本通讯的目的是公开一种合成萨拉戈齐酸 C (1)5 的途径，该途径适用于该天然产物家族其他成员的合成。 6
• 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：——