(S)-2-(tert-butyldimethylsilyloxy)-2-((4S,5R)-5-((R)-(methoxymethoxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde | 1018751-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-(tert-butyldimethylsilyloxy)-2-((4S,5R)-5-((R)-(methoxymethoxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde
• 英文别名: (2R)-2-[tert-butyl(dimethyl)silyl]oxy-2-[(4S,5R)-5-[(R)-methoxymethoxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde
• CAS: 1018751-03-5
• 化学式: C₂₂H₃₆O₆Si
• 分子量: 424.61
• InChiKey: DNSRRAWPLGJOND-MTQWCTHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-butyldimethylsilyloxy)-2-((4S,5R)-5-((R)-(methoxymethoxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde 、 烯丙基溴化镁 在 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 反应 0.08h， 以91%的产率得到((1S)-2-hydroxy-1-((4S,5R)-5-((R)-(methoxymethoxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enyloxy)(tert-butyl)dimethylsilaneacetaldehyde
  参考文献：
  名称：

  Stereoselective Total Synthesis of (+)-Cardiobutanolide

  摘要：

  Stereoselective synthesis of styryllactone (+)-cardiobutanolide was accomplished in good overall yield from D-(-)-tartaric acid. Key features of the synthesis include the elaboration of a gamma-hydroxy butyramide obtained from the dimethylarnide of tartaric acid, involving a combination of the addition of 1,3-dithian-2-yllithium and stereoselective reduction.

  DOI：

  10.1021/jo7025614
• 作为产物：
  描述：

  ((R)-(1,3-dithian-2-yl)((4S,5R)-5-((R)-(methoxymethoxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)dimethylsilane 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以94%的产率得到(S)-2-(tert-butyldimethylsilyloxy)-2-((4S,5R)-5-((R)-(methoxymethoxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde
  参考文献：
  名称：

  Stereoselective Total Synthesis of (+)-Cardiobutanolide

  摘要：

  Stereoselective synthesis of styryllactone (+)-cardiobutanolide was accomplished in good overall yield from D-(-)-tartaric acid. Key features of the synthesis include the elaboration of a gamma-hydroxy butyramide obtained from the dimethylarnide of tartaric acid, involving a combination of the addition of 1,3-dithian-2-yllithium and stereoselective reduction.

  DOI：

  10.1021/jo7025614

文献信息

• Stereoselective Total Synthesis of (+)-Cardiobutanolide
  作者：Kavirayani R. Prasad、Shivajirao L. Gholap

  DOI：10.1021/jo7025614

  日期：2008.4.1

  Stereoselective synthesis of styryllactone (+)-cardiobutanolide was accomplished in good overall yield from D-(-)-tartaric acid. Key features of the synthesis include the elaboration of a gamma-hydroxy butyramide obtained from the dimethylarnide of tartaric acid, involving a combination of the addition of 1,3-dithian-2-yllithium and stereoselective reduction.