(4R,1'R,2'R,3'R,5'R,1''S)-4-methoxymethoxy-oct-7-enoic acid 1-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-3'-(methoxy-methyl-carbamoyl)-propyl ester | 865091-24-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R,1'R,2'R,3'R,5'R,1''S)-4-methoxymethoxy-oct-7-enoic acid 1-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-3'-(methoxy-methyl-carbamoyl)-propyl ester
• 英文别名: [(1R)-1-[(2R,5R)-5-[(1S)-1-(methoxymethoxy)pentadecyl]oxolan-2-yl]-4-[methoxy(methyl)amino]-4-oxobutyl] (4R)-4-(methoxymethoxy)oct-7-enoate
• CAS: 865091-24-3
• 化学式: C₃₇H₆₉NO₉
• 分子量: 671.956
• InChiKey: NBJAVPIRNPLBNN-UODCSFEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  47
• 可旋转键数：
  33
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (4R,1'R,2'R,3'R,5'R,1''S)-4-methoxymethoxy-oct-7-enoic acid 1-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-3'-(methoxy-methyl-carbamoyl)-propyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium on activated charcoal 氢气 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 (+)-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 16.0h， 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：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 吡啶 、 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium chlorite 、 dimethyl sulfide borane 、 NaH₂PO₄ buffer 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 反应 158.0h， 生成 (4R,1'R,2'R,3'R,5'R,1''S)-4-methoxymethoxy-oct-7-enoic acid 1-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-3'-(methoxy-methyl-carbamoyl)-propyl ester
  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.