(4R,2'R,5'R,1''S)-N-methoxy-4-hydroxy-4-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-N-methyl-butyramide | 865091-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (4R,2'R,5'R,1''S)-N-methoxy-4-hydroxy-4-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-N-methyl-butyramide
• 英文别名: (4R)-4-hydroxy-N-methoxy-4-[(2R,5R)-5-[(1S)-1-(methoxymethoxy)pentadecyl]oxolan-2-yl]-N-methylbutanamide
• CAS: 865091-21-0
• 化学式: C₂₇H₅₃NO₆
• 分子量: 487.721
• InChiKey: SNQONYAIHASVSS-FXSWLTOZSA-N

物化性质

• 沸点：
  567.5±58.0 °C(predicted)
• 密度：
  1.004±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,2'R,5'R,1''S)-N-methoxy-4-hydroxy-4-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-N-methyl-butyramide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 (+)-B-methoxydiisocamphenylborane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 31.0h， 生成 (5R,11R,14R,2'R,5'R,1''S)-5,11-bis(methoxymethoxy)-14-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-oxacyclotetradecan-2-one
  参考文献：
  名称：

  Total Synthesis and Structural Confirmation of (+)-Longicin

  摘要：

  A stereocontrolled total synthesis of (+)-longicin, a representative of the class of mono-THF-acetogenins, is described. The strategy involves the utilization of D- and L-glutamic acids as chirons that correspond to two five-carbon segments harboring stereogenic centers at C4 and at C17 of the C-32 polyketide-derived natural product. The use of Grubbs' RCM reaction as a novel "chain elongation" strategy for the synthesis of acetogenin-type structures and a new protocol for butenolide incorporation are also described.

  DOI：

  10.1021/ol051483k
• 作为产物：
  描述：

  2-R-5-氧四氢呋喃－2－羧酰氯 在 palladium on activated charcoal 4-二甲氨基吡啶 、 三氟化硼乙醚 、 氢气 、 三正丁基氢锡 、 二甲基氯化铝 、 silica gel 、 四丁基碘化铵 、 二异丁基氢化铝 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， -100.0~20.0 ℃ 、101.33 kPa 条件下， 反应 149.0h， 生成 (4R,2'R,5'R,1''S)-N-methoxy-4-hydroxy-4-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-N-methyl-butyramide
  参考文献：
  名称：

  Total Synthesis and Structural Confirmation of (+)-Longicin

  摘要：

  A stereocontrolled total synthesis of (+)-longicin, a representative of the class of mono-THF-acetogenins, is described. The strategy involves the utilization of D- and L-glutamic acids as chirons that correspond to two five-carbon segments harboring stereogenic centers at C4 and at C17 of the C-32 polyketide-derived natural product. The use of Grubbs' RCM reaction as a novel "chain elongation" strategy for the synthesis of acetogenin-type structures and a new protocol for butenolide incorporation are also described.

  DOI：

  10.1021/ol051483k

文献信息

• Total Synthesis and Structural Confirmation of (+)-Longicin
  作者：Stephen Hanessian、Simon Giroux、Maxime Buffat

  DOI：10.1021/ol051483k

  日期：2005.9.1

  A stereocontrolled total synthesis of (+)-longicin, a representative of the class of mono-THF-acetogenins, is described. The strategy involves the utilization of D- and L-glutamic acids as chirons that correspond to two five-carbon segments harboring stereogenic centers at C4 and at C17 of the C-32 polyketide-derived natural product. The use of Grubbs' RCM reaction as a novel "chain elongation" strategy for the synthesis of acetogenin-type structures and a new protocol for butenolide incorporation are also described.