(3S)-3-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-3-methoxy-2,2-dimethylpropanal | 168072-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-3-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-3-methoxy-2,2-dimethylpropanal
• CAS: 168072-66-0
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: ZDPVZOJCGPNMNI-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-3-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-3-methoxy-2,2-dimethylpropanal 在 吡啶 、 sodium hydroxide 、 正丁基锂 、 水 、 sodium acetate 、 一溴化碘 、 四氯化钛 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-[(2R,4S)-4-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-methoxy-3,3-dimethyl-butyl]-[1,3]dioxolan-2-one
  参考文献：
  名称：

  Diastereoselective synthesis of N-benzoyl mycalamine, the fully elaborated trioxadecalin nucleus of mycalamide. A. Control of the key N-acyl aminal stereocenter via carbamate acylation

  摘要：

  A highly diastereoselective synthesis of N-benzoyl mycalamine (8), corresponding to the C(10)-C(18) amine fragment of mycalamide A, is described. The synthesis features a highly stereoselective acylation of carbamate 7 that permits the stereochemistry of the key C(10)-N-acyl aminal center to be controlled.

  DOI：

  10.1016/0040-4039(95)00093-r
• 作为产物：
  描述：

  (R)-2,2-Diethyl-4-((S)-1-methoxy-2,2-dimethyl-but-3-enyl)-[1,3]dioxolane 在 臭氧 、 三苯基膦 作用下， 生成 (3S)-3-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-3-methoxy-2,2-dimethylpropanal
  参考文献：
  名称：

  Diastereoselective synthesis of N-benzoyl mycalamine, the fully elaborated trioxadecalin nucleus of mycalamide. A. Control of the key N-acyl aminal stereocenter via carbamate acylation

  摘要：

  A highly diastereoselective synthesis of N-benzoyl mycalamine (8), corresponding to the C(10)-C(18) amine fragment of mycalamide A, is described. The synthesis features a highly stereoselective acylation of carbamate 7 that permits the stereochemistry of the key C(10)-N-acyl aminal center to be controlled.

  DOI：

  10.1016/0040-4039(95)00093-r

文献信息

• Diastereoselective synthesis of N-benzoyl mycalamine, the fully elaborated trioxadecalin nucleus of mycalamide. A. Control of the key N-acyl aminal stereocenter via carbamate acylation
  作者：Thomas G. Marron、William R. Roush

  DOI：10.1016/0040-4039(95)00093-r

  日期：1995.3

  A highly diastereoselective synthesis of N-benzoyl mycalamine (8), corresponding to the C(10)-C(18) amine fragment of mycalamide A, is described. The synthesis features a highly stereoselective acylation of carbamate 7 that permits the stereochemistry of the key C(10)-N-acyl aminal center to be controlled.