(6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol | 691905-78-9

• 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: (6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol
• 英文别名: tert-butyl allyl((2S,3S,4R,5R,E)-1,2,3,4-tetrahydroxy-7-phenylpent-6-en-5-yl)carbamate；tert-butyl N-prop-2-enyl-N-[(E,3R,4R,5S,6S)-4,5,6,7-tetrahydroxy-1-phenylhept-1-en-3-yl]carbamate
• CAS: 691905-78-9
• 化学式: C₂₁H₃₁NO₆
• 分子量: 393.48
• InChiKey: CIOILSJQTZHNKP-QVKHROGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol 在 Grubbs catalyst first generation 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 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
• 作为产物：
  描述：

  L-木糖 在 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 35.0h， 生成 (6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol
  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

• Total Synthesis of Uniflorine A, Casuarine, Australine, 3-<i>epi</i>-Australine, and 3,7-Di-<i>epi</i>-australine from a Common Precursor
  作者：Thunwadee Ritthiwigrom、Anthony C. Willis、Stephen G. Pyne

  DOI：10.1021/jo902355p

  日期：2010.2.5

  A flexible method for the diastereoselective total synthesis of the pyrrolizidine alkaloids uniflorine A, casuarine, australine, and 3-epi-australine and the unnatural epimer 3,7-di-epi-australine from a common chiral 2,5-dihydropyrrole precursor is described.

  描述了一种灵活的方法，可从一种常见的手性2,5-二氢吡咯前体非对映选择性地合成吡咯烷核生物碱单花碱A，木麻黄，奥曲林和3- Epi- australine和非天然差向异构体3,7-di- epi - australine 。
• 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.