tert-butyl (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(1R,2S,3S)-1,2,3-tris(benzyloxy)-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate | 691905-82-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: tert-butyl (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(1R,2S,3S)-1,2,3-tris(benzyloxy)-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2R,3S,4R)-3,4-bis(phenylmethoxy)-2-[(1R,2S,3S)-1,2,3-tris(phenylmethoxy)-4-trityloxybutyl]pyrrolidine-1-carboxylate
• CAS: 691905-82-5
• 化学式: C₆₇H₆₉NO₈
• 分子量: 1016.29
• InChiKey: LAEHELNJMKPYBO-LESODZMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  76
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(1R,2S,3S)-1,2,3-tris(benzyloxy)-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以54%的产率得到(1S,2R,6S,7R,8R,8aR)-1,2,6,7,8-pentakis(benzyloxy)octahydroindolizine
  参考文献：
  名称：

  Synthesis of Putative Uniflorine A

  摘要：

  A diastereoselective synthesis of the putative structure of the natural product uniflorine A has been achieved by using the Petasis borono-Mannich reaction and ring-closing metathesis as key steps. The NMR data of the synthetic material did not match that reported for the natural product. The structure of the final synthetic product was unequivocally determined by single-crystal X-ray study of its pentaacetate derivative. Thus it was concluded that the proposed structure of uniflorine A is incorrect.

  DOI：

  10.1021/jo049806y
• 作为产物：
  描述：

  L-木糖 在 potassium osmate(VI) 、 Grubbs catalyst first generation 吡啶 、 四丁基碘化铵 、 sodium hydride 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 173.0h， 生成 tert-butyl (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(1R,2S,3S)-1,2,3-tris(benzyloxy)-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Putative Uniflorine A

  摘要：

  A diastereoselective synthesis of the putative structure of the natural product uniflorine A has been achieved by using the Petasis borono-Mannich reaction and ring-closing metathesis as key steps. The NMR data of the synthetic material did not match that reported for the natural product. The structure of the final synthetic product was unequivocally determined by single-crystal X-ray study of its pentaacetate derivative. Thus it was concluded that the proposed structure of uniflorine A is incorrect.

  DOI：

  10.1021/jo049806y

文献信息

• Synthesis of Putative Uniflorine A
  作者：Andrew S. Davis、Stephen G. Pyne、Brian W. Skelton、Allan H. White

  DOI：10.1021/jo049806y

  日期：2004.4.1

  A diastereoselective synthesis of the putative structure of the natural product uniflorine A has been achieved by using the Petasis borono-Mannich reaction and ring-closing metathesis as key steps. The NMR data of the synthetic material did not match that reported for the natural product. The structure of the final synthetic product was unequivocally determined by single-crystal X-ray study of its pentaacetate derivative. Thus it was concluded that the proposed structure of uniflorine A is incorrect.