(R)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropionic acid methyl ester | 895532-48-6

• 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: (R)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropionic acid methyl ester
• 英文别名: (R)-3-[(R)-2,2-dimethyl[1,3]dioxolan-4-yl]-2,2-dimethyl-3-hydroxypropionic acid methyl ester；methyl (3R)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2,2-dimethylpropanoate
• CAS: 895532-48-6
• 化学式: C₁₁H₂₀O₅
• 分子量: 232.277
• InChiKey: PDLYMQHTWHUGCZ-SFYZADRCSA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  318.3±22.0 °C(predicted)
• 密度：
  1.096±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropionic acid methyl ester 在 lithium aluminium tetrahydride 、 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 (3R)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3-phenylmethoxypropanal
  参考文献：
  名称：

  In Pursuit of Pestalotiopsin A via Zirconocene-Mediated Ring Contraction

  摘要：

  [graphics]An asymmetric route from the epimeric,- hydroxy esters 4 and 5 to the densely functionalized (+)-10 and (-)-10, respectively, is described. Either cyclobutanol can be made available as the predominant product. The levorotatory antipode has been transformed into the advanced intermediate 21 bearing side chains destined to become incorporated into the cyclononene ring of the title compound (1).

  DOI：

  10.1021/ol060827j
• 作为产物：
  描述：

  异丁酸甲酯 在 甲醇 、 正丁基锂 、 potassium carbonate 、 二异丙胺 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 61.0h， 生成 (R)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropionic acid methyl ester
  参考文献：
  名称：

  In Pursuit of Pestalotiopsin A via Zirconocene-Mediated Ring Contraction

  摘要：

  [graphics]An asymmetric route from the epimeric,- hydroxy esters 4 and 5 to the densely functionalized (+)-10 and (-)-10, respectively, is described. Either cyclobutanol can be made available as the predominant product. The levorotatory antipode has been transformed into the advanced intermediate 21 bearing side chains destined to become incorporated into the cyclononene ring of the title compound (1).

  DOI：

  10.1021/ol060827j

文献信息

• In Pursuit of Pestalotiopsin A via Zirconocene-Mediated Ring Contraction
  作者：Shuzhi Dong、Gregory D. Parker、Takahiro Tei、Leo A. Paquette

  DOI：10.1021/ol060827j

  日期：2006.5.1

  [graphics]An asymmetric route from the epimeric,- hydroxy esters 4 and 5 to the densely functionalized (+)-10 and (-)-10, respectively, is described. Either cyclobutanol can be made available as the predominant product. The levorotatory antipode has been transformed into the advanced intermediate 21 bearing side chains destined to become incorporated into the cyclononene ring of the title compound (1).
• Pestalotiopsin A. Enantioselective Construction of Potential Building Blocks Derived from Antipodal Cyclobutanol Intermediates
  作者：Leo A. Paquette、Gregory D. Parker、Takahiro Tei、Shuzhi Dong

  DOI：10.1021/jo070861r

  日期：2007.9.1

  [GRAPHICS]D-Glyceraldehyde acetonide has been used as the starting point for accessing the enantiomeric cyclobutanols 11 in optically pure condition. The dextrorotatory enantiomer has been transformed in five steps into the [3.2.0] bicyclic lactone 22. While the deoxygenation of 22 proved to be problematical, the uncyclized variant 25 underwent the Barton process smoothly. These findings guided the related conversion of (-)-11 into 34. Use was also made of ring-closing metathesis to bring about the conversion of (+)-11 into [4.2.0] bicyclic lactone building blocks. In general, all three pathways are efficient and offer the prospect of practical side-chain appendage for the purpose of installing the nine-membered ring of pestalotiopsin A (1).