tert-butyl (2R)-2-[(2S,3S)-4-(triphenylmethyloxy)-1,2,3-trihydroxybutyl]-2,5-dihydro-1H-pyrrole-1-carboxylate | 691905-80-3

• 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)-2-[(2S,3S)-4-(triphenylmethyloxy)-1,2,3-trihydroxybutyl]-2,5-dihydro-1H-pyrrole-1-carboxylate
• 英文别名: tert-butyl (2R)-2-[(1R,2S,3S)-1,2,3-trihydroxy-4-trityloxybutyl]-2,5-dihydropyrrole-1-carboxylate
• CAS: 691905-80-3
• 化学式: C₃₂H₃₇NO₆
• 分子量: 531.649
• InChiKey: MHEPLDRVTWKBIS-VJLHXPKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  99.5
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R)-2-[(2S,3S)-4-(triphenylmethyloxy)-1,2,3-trihydroxybutyl]-2,5-dihydro-1H-pyrrole-1-carboxylate 在 potassium osmate(VI) 四丁基碘化铵 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 102.0h， 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
• 作为产物：
  描述：

  L-木糖 在 Grubbs catalyst first generation 吡啶 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 71.0h， 生成 tert-butyl (2R)-2-[(2S,3S)-4-(triphenylmethyloxy)-1,2,3-trihydroxybutyl]-2,5-dihydro-1H-pyrrole-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

• Synthetic and spectroscopic studies on the structures of uniflorines A and B: structural revision to 1,2,6,7-tetrahydroxy-3-hydroxymethylpyrrolizidine alkaloids
  作者：Andrew S. Davis、Thunwadee Ritthiwigrom、Stephen G. Pyne

  DOI：10.1016/j.tet.2008.02.110

  日期：2008.5

  diastereoselective synthesis of the C-2 epimer and the C-1, C-2 di-epimers of the putative structure of the alkaloid uniflorine A has been achieved. The synthesis of the latter di-epimers employed a novel pyrrolo[1,2-c]oxazin-1-one precursor to allow for the reversal of π-facial diastereoselectivity in an osmium(VIII)-catalyzed syn-dihydroxylation (DH) reaction. The NMR spectral data of these epimeric compounds

  已经实现了生物碱单花碱A的推定结构的C-2差向异构体和C-1，C-2二表位异构体的非对映选择性合成。后者二差向异构体的合成中使用的新颖的吡咯并[1,2- c ^ ]恶嗪-1-酮的前体，以允许π面部非对映选择性的逆转在锇（VIII） -催化顺-二羟基化（DH）反应。这些差向异构化合物和相关异构体的NMR光谱数据与天然产物的NMR光谱数据不匹配。通过将单花素A和B与木麻黄素和已知的合成的1,2,6,7-四羟基-3-羟甲基吡咯烷核苷异构体的NMR数据进行比较，我们明确地得出结论，单花素B是已知的生物碱木麻黄。尽管我们无法通过原始材料和数据明确证明单花青素A的结构，但已发表的数据表明，天然产物也是具有相同相对C-的1,2,6,7-四羟基-3-羟甲基吡咯烷核苷7–C-7a–C-1–C-2–C-3立体化学为木麻黄。因此，我们认为单花青素A是6-表位-酪氨酸。
• 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.