tert-butyl (4S)-4-((2R,6R)-6-(2-(4-methoxybenzyloxy)ethyl)-4-oxo-tetrahydro-2H-pyran-2-yl)-2,2-dimethyloxazolidine-3-carboxylate | 1231934-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (4S)-4-((2R,6R)-6-(2-(4-methoxybenzyloxy)ethyl)-4-oxo-tetrahydro-2H-pyran-2-yl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-4-[(2R,6R)-6-[2-[(4-methoxyphenyl)methoxy]ethyl]-4-oxooxan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1231934-46-5
• 化学式: C₂₅H₃₇NO₇
• 分子量: 463.571
• InChiKey: WWAIADJHXIERPD-BHIFYINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-4-((2R,6R)-6-(2-(4-methoxybenzyloxy)ethyl)-4-oxo-tetrahydro-2H-pyran-2-yl)-2,2-dimethyloxazolidine-3-carboxylate 、 乙酸酐 在 sodium tetrahydroborate 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 以75%的产率得到
  参考文献：
  名称：

  Insights into the stereoselective BF3-catalyzed hetero Diels–Alder reaction of Garner’s aldehyde with Danishefsky’s diene

  摘要：

  A trans-2,6-disubstituted tetrahydropyranone was prepared in high yield via a BF3-mediated hetero Diels-Alder reaction between Danishefsky's diene and Garner's aldehyde. Only two of the four possible reaction products were obtained, and excellent diastereoselectivity toward the exo-syn adduct was observed (de = 80%). The origin of this somewhat unusual selectivity can be attributed to the steric interactions between the bulky protecting groups present in the diene and dienophile. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.028
• 作为产物：
  描述：

  tert-butyl (4S)-4-((2R,6R)-4-(tert-butyldimethylsilyloxy)-6-(2-(4-methoxybenzyloxy)ethyl)-3,6-dihydro-2H-pyran-2-yl)-2,2-dimethyloxazolidine-3-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 tert-butyl (4S)-4-((2R,6R)-6-(2-(4-methoxybenzyloxy)ethyl)-4-oxo-tetrahydro-2H-pyran-2-yl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Insights into the stereoselective BF3-catalyzed hetero Diels–Alder reaction of Garner’s aldehyde with Danishefsky’s diene

  摘要：

  A trans-2,6-disubstituted tetrahydropyranone was prepared in high yield via a BF3-mediated hetero Diels-Alder reaction between Danishefsky's diene and Garner's aldehyde. Only two of the four possible reaction products were obtained, and excellent diastereoselectivity toward the exo-syn adduct was observed (de = 80%). The origin of this somewhat unusual selectivity can be attributed to the steric interactions between the bulky protecting groups present in the diene and dienophile. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.028