TBS-Hmb-MeVal-MeVal-(4-O-TBS)(3-O-MOM)Dhmp-Lar | 1236783-91-7

• 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: TBS-Hmb-MeVal-MeVal-(4-O-TBS)(3-O-MOM)Dhmp-Lar
• 英文别名: [(1S,4S,4aS,6S,8aS)-4-hydroxy-4,8a-dimethyl-6-prop-1-en-2-yl-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl] (2S,3S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-methylbutanoyl]-methylamino]-3-methylbutanoyl]-methylamino]-3-methylbutanoyl]-3-(methoxymethoxy)-3-methylpyrrolidine-2-carboxylate
• CAS: 1236783-91-7
• 化学式: C₅₂H₉₇N₃O₁₀Si₂
• 分子量: 980.527
• InChiKey: PLROHGSZMCMPIQ-BCLIACSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.43
• 重原子数：
  67
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  TBS-Hmb-MeVal-MeVal-(4-O-TBS)(3-O-MOM)Dhmp-Lar 在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Total Synthesis of Depsilairdin

  摘要：

  The total synthesis of depsilairdin, a host-selective phytotoxin isolated from Leptosphaeria maculans (the causal agent of blackleg disease of oilseed Brassicas), has been achieved by N-terminal extension of a suitably protected derivative of the hitherto unknown amino acid (2S,3S,4R)-3,4-dihydroxy-3-methyl-proline (Dhmp) followed by esterification with lairdinol A. The latter esterification, complicated by the sterically hindered nature of the carboxyl group, was accomplished by a novel method involving reaction of the 1-hydroxybenzotriazole (HOBt) derived active ester with the bromomagnesium alkoxide of lairdinol A. Three depsilairdin analogues were also prepared by replacing the Dhmp residue with L-proline and cis- and trans-4-hydroxy-L-proline. Phytotoxicity assays showed that the analogues were nontoxic to both blackleg-susceptible (brown mustard) and -resistant (canola) plants, suggesting that the presence of the Dhmp residue in depsilairdin is important for its host-selective toxicity toward brown mustard.

  DOI：

  10.1021/jo1009239
• 作为产物：
  描述：

  lairdinol A 、 TBS-Hmb-MeVal-MeVal-(4-O-TBS)(3-O-MOM)Dhmp-OBt 在 苯基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以40%的产率得到TBS-Hmb-MeVal-MeVal-(4-O-TBS)(3-O-MOM)Dhmp-Lar
  参考文献：
  名称：

  Total Synthesis of Depsilairdin

  摘要：

  The total synthesis of depsilairdin, a host-selective phytotoxin isolated from Leptosphaeria maculans (the causal agent of blackleg disease of oilseed Brassicas), has been achieved by N-terminal extension of a suitably protected derivative of the hitherto unknown amino acid (2S,3S,4R)-3,4-dihydroxy-3-methyl-proline (Dhmp) followed by esterification with lairdinol A. The latter esterification, complicated by the sterically hindered nature of the carboxyl group, was accomplished by a novel method involving reaction of the 1-hydroxybenzotriazole (HOBt) derived active ester with the bromomagnesium alkoxide of lairdinol A. Three depsilairdin analogues were also prepared by replacing the Dhmp residue with L-proline and cis- and trans-4-hydroxy-L-proline. Phytotoxicity assays showed that the analogues were nontoxic to both blackleg-susceptible (brown mustard) and -resistant (canola) plants, suggesting that the presence of the Dhmp residue in depsilairdin is important for its host-selective toxicity toward brown mustard.

  DOI：

  10.1021/jo1009239