(2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-amino-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine | 219914-03-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-amino-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine
• 英文别名: (2S)-2-[[(2S,3Z,5S,6E,8R)-8-amino-2-benzyl-9-(methoxycarbonyldisulfanyl)-5-propan-2-ylnona-3,6-dienoyl]amino]-4-methylsulfanylbutanoic acid
• CAS: 219914-03-1
• 化学式: C₂₆H₃₈N₂O₅S₃
• 分子量: 554.796
• InChiKey: JROKNTVYGWFMIN-VZKYLMKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  36
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  195
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-amino-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine 在 水 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到(2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-amino-9-mercapto-2,6-nonadienyl methionine
  参考文献：
  名称：

  Synthesis of Sulfur-Containing Olefinic Peptide Mimetic Farnesyl Transferase Inhibitors Using the Nozaki−Hiyama−Kishi Reaction and Cuprate S_N2‘ Displacements

  摘要：

  Syntheses of the potent sulfur-containing tetrapeptide mimetic farnesyl transferase inhibitors B956 (22) and B957 (23) are described. The two double bonds in 22 and 23 were constructed by application of iterative NHK and cuprate S(N)2' reactions. Normal syn NHK reaction and substrate-dependent syn and anti-S(N)2' diastereoselectivities accompanied by exclusive E-olefin selectivity were observed for the first NHK iteration (1 --> 4). In the second iteration, unexpected epimerization and a strong preference for syn diastereoselectivity was observed for the NHK reaction (5b --> 7a + 9a) while an unusual Z-olefin was observed for the S(N)2' reaction (7b --> 11). Deprotection conditions were optimized to ensure high purity and yield of the final aminothiol compounds.

  DOI：

  10.1021/jo981892c
• 作为产物：
  描述：

  (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid 在 N-甲基吗啉 、 盐酸 、 lithium hydroxide 、 sodium acetate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-amino-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine
  参考文献：
  名称：

  Synthesis of Sulfur-Containing Olefinic Peptide Mimetic Farnesyl Transferase Inhibitors Using the Nozaki−Hiyama−Kishi Reaction and Cuprate S_N2‘ Displacements

  摘要：

  Syntheses of the potent sulfur-containing tetrapeptide mimetic farnesyl transferase inhibitors B956 (22) and B957 (23) are described. The two double bonds in 22 and 23 were constructed by application of iterative NHK and cuprate S(N)2' reactions. Normal syn NHK reaction and substrate-dependent syn and anti-S(N)2' diastereoselectivities accompanied by exclusive E-olefin selectivity were observed for the first NHK iteration (1 --> 4). In the second iteration, unexpected epimerization and a strong preference for syn diastereoselectivity was observed for the NHK reaction (5b --> 7a + 9a) while an unusual Z-olefin was observed for the S(N)2' reaction (7b --> 11). Deprotection conditions were optimized to ensure high purity and yield of the final aminothiol compounds.

  DOI：

  10.1021/jo981892c

文献信息

• Synthesis of Sulfur-Containing Olefinic Peptide Mimetic Farnesyl Transferase Inhibitors Using the Nozaki−Hiyama−Kishi Reaction and Cuprate S_N2‘ Displacements
  作者：Hu Yang、Xiaoning C. Sheng、Edmund M. Harrington、Karen Ackermann、Ana Maria Garcia、Michael D. Lewis

  DOI：10.1021/jo981892c

  日期：1999.1.1

  Syntheses of the potent sulfur-containing tetrapeptide mimetic farnesyl transferase inhibitors B956 (22) and B957 (23) are described. The two double bonds in 22 and 23 were constructed by application of iterative NHK and cuprate S(N)2' reactions. Normal syn NHK reaction and substrate-dependent syn and anti-S(N)2' diastereoselectivities accompanied by exclusive E-olefin selectivity were observed for the first NHK iteration (1 --> 4). In the second iteration, unexpected epimerization and a strong preference for syn diastereoselectivity was observed for the NHK reaction (5b --> 7a + 9a) while an unusual Z-olefin was observed for the S(N)2' reaction (7b --> 11). Deprotection conditions were optimized to ensure high purity and yield of the final aminothiol compounds.