4-[(3E,2'S,3'S,4'R,5'R)-5'-(benzoyloxymethyl)-3',4'-bis(benzyloxy)-N'-(tert-butyloxycarbonyl)pyrrolidin-2'-yl]but-3-en-2-one | 1229597-85-6

• 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: 4-[(3E,2'S,3'S,4'R,5'R)-5'-(benzoyloxymethyl)-3',4'-bis(benzyloxy)-N'-(tert-butyloxycarbonyl)pyrrolidin-2'-yl]but-3-en-2-one
• 英文别名: tert-butyl (2R,3R,4S,5S)-2-(benzoyloxymethyl)-5-[(E)-3-oxobut-1-enyl]-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate
• CAS: 1229597-85-6
• 化学式: C₃₅H₃₉NO₇
• 分子量: 585.697
• InChiKey: YCTFDAWIEREBRK-XKAXWABESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[(3E,2'S,3'S,4'R,5'R)-5'-(benzoyloxymethyl)-3',4'-bis(benzyloxy)-N'-(tert-butyloxycarbonyl)pyrrolidin-2'-yl]but-3-en-2-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Total synthesis of natural (+)-hyacinthacine A6 and non-natural (+)-7a-epi-hyacinthacine A1 and (+)-5,7a-diepi-hyacinthacine A6

  摘要：

  Naturally occurring (1S,2R,3R,5R,7aR)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine [(+)-hyacinthacine A(6), 2] together with unnatural (1S,2R,3R,7aS)-1,2-dihydroxy-3-hydroxy-methylpyrrolizidine [(+)-7a-epi-hyacinthacine A(1), 3] and (1S,2R,3R,5S,7aS)-1,2-dihydroxy-3-hydroxy-methyl-5-methylpyrrolizidine [(+)-5,7a-diepi-hyacinthacine A(6), 4] have been synthesized from a DALDP derivative [5, (2R,35,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-pyrrolidine], as the homochiral starting material. The synthetic process employed took advantages of Wittig methodology followed by internal lactamization, in the case of (+)-7a-epi-hyacinthacine A(1) (3), and reductive amination for (+)-hyacinthacine A(6) (2) and (+)-5,7a-diepi-hyacinthacine A(6) (4). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.049
• 作为产物：
  描述：

  tert-butyl (2R,3R,4S,5S)-2-(benzoyloxymethyl)-5-formyl-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate 、 1-三苯基膦-2-丙酮 以 甲苯 为溶剂， 反应 8.0h， 以600 mg的产率得到4-[(3E,2'S,3'S,4'R,5'R)-5'-(benzoyloxymethyl)-3',4'-bis(benzyloxy)-N'-(tert-butyloxycarbonyl)pyrrolidin-2'-yl]but-3-en-2-one
  参考文献：
  名称：

  Total synthesis of natural (+)-hyacinthacine A6 and non-natural (+)-7a-epi-hyacinthacine A1 and (+)-5,7a-diepi-hyacinthacine A6

  摘要：

  Naturally occurring (1S,2R,3R,5R,7aR)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine [(+)-hyacinthacine A(6), 2] together with unnatural (1S,2R,3R,7aS)-1,2-dihydroxy-3-hydroxy-methylpyrrolizidine [(+)-7a-epi-hyacinthacine A(1), 3] and (1S,2R,3R,5S,7aS)-1,2-dihydroxy-3-hydroxy-methyl-5-methylpyrrolizidine [(+)-5,7a-diepi-hyacinthacine A(6), 4] have been synthesized from a DALDP derivative [5, (2R,35,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-pyrrolidine], as the homochiral starting material. The synthetic process employed took advantages of Wittig methodology followed by internal lactamization, in the case of (+)-7a-epi-hyacinthacine A(1) (3), and reductive amination for (+)-hyacinthacine A(6) (2) and (+)-5,7a-diepi-hyacinthacine A(6) (4). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.049

文献信息

• Total synthesis of natural (+)-hyacinthacine A6 and non-natural (+)-7a-epi-hyacinthacine A1 and (+)-5,7a-diepi-hyacinthacine A6
  作者：Isidoro Izquierdo、María T. Plaza、Juan A. Tamayo、Francisco Franco、Fernando Sánchez-Cantalejo

  DOI：10.1016/j.tet.2010.03.049

  日期：2010.5

  Naturally occurring (1S,2R,3R,5R,7aR)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine [(+)-hyacinthacine A(6), 2] together with unnatural (1S,2R,3R,7aS)-1,2-dihydroxy-3-hydroxy-methylpyrrolizidine [(+)-7a-epi-hyacinthacine A(1), 3] and (1S,2R,3R,5S,7aS)-1,2-dihydroxy-3-hydroxy-methyl-5-methylpyrrolizidine [(+)-5,7a-diepi-hyacinthacine A(6), 4] have been synthesized from a DALDP derivative [5, (2R,35,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-pyrrolidine], as the homochiral starting material. The synthetic process employed took advantages of Wittig methodology followed by internal lactamization, in the case of (+)-7a-epi-hyacinthacine A(1) (3), and reductive amination for (+)-hyacinthacine A(6) (2) and (+)-5,7a-diepi-hyacinthacine A(6) (4). (C) 2010 Elsevier Ltd. All rights reserved.