(2'S,3'R,4'E,6'E,8'S,9'S,4S)-4-benzyl-3-[3'-hydroxy-9'-methoxy-2',6',8'-trimethyl-10'-phenyl-4,6-decadienoyl]-oxazolin-2-one | 298202-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2'S,3'R,4'E,6'E,8'S,9'S,4S)-4-benzyl-3-[3'-hydroxy-9'-methoxy-2',6',8'-trimethyl-10'-phenyl-4,6-decadienoyl]-oxazolin-2-one
• 英文别名: (4S)-4-benzyl-3-[(2S,3R,4E,6E,8S,9S)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl]-1,3-oxazolidin-2-one
• CAS: 298202-09-2
• 化学式: C₃₀H₃₇NO₅
• 分子量: 491.627
• InChiKey: KNHBJFWJMBGQGD-SQLVACEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2'S,3'R,4'E,6'E,8'S,9'S,4S)-4-benzyl-3-[3'-hydroxy-9'-methoxy-2',6',8'-trimethyl-10'-phenyl-4,6-decadienoyl]-oxazolin-2-one 在 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (3S,4S)-3-((1E,3E)-(5S,6S)-6-Methoxy-3,5-dimethyl-7-phenyl-hepta-1,3-dienyl)-4-methyl-5-oxo-isoxazolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantiospecific Synthesis of N-Boc-Adda:  A Linear Approach

  摘要：

  Synthesis of the unusual amino acid (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6 decadienoic acid (Adda), a unit of numerous cyanobacterial toxins, is described. Construction of the target molecule was achieved in 13 steps with an overall yield of 40%. The work is highlighted by a novel one-pot transformation from isoxazolidin-5-one intermediate 6 to the final product, a step that can also be used to form beta-amino acids.

  DOI：

  10.1021/ol006347o
• 作为产物：
  描述：

  ethyl(2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenyl-2-hexenoate 在 manganese(IV) oxide 、 三氟甲磺酸二丁硼 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 55.58h， 生成 (2'S,3'R,4'E,6'E,8'S,9'S,4S)-4-benzyl-3-[3'-hydroxy-9'-methoxy-2',6',8'-trimethyl-10'-phenyl-4,6-decadienoyl]-oxazolin-2-one
  参考文献：
  名称：

  Enantiospecific Synthesis of N-Boc-Adda:  A Linear Approach

  摘要：

  Synthesis of the unusual amino acid (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6 decadienoic acid (Adda), a unit of numerous cyanobacterial toxins, is described. Construction of the target molecule was achieved in 13 steps with an overall yield of 40%. The work is highlighted by a novel one-pot transformation from isoxazolidin-5-one intermediate 6 to the final product, a step that can also be used to form beta-amino acids.

  DOI：

  10.1021/ol006347o

文献信息

• Enantiospecific Synthesis of <i>N</i>-Boc-Adda:  A Linear Approach
  作者：Clay Pearson、Kenneth L. Rinehart、Michihiro Sugano、Jennifer R. Costerison

  DOI：10.1021/ol006347o

  日期：2000.9.1

  Synthesis of the unusual amino acid (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6 decadienoic acid (Adda), a unit of numerous cyanobacterial toxins, is described. Construction of the target molecule was achieved in 13 steps with an overall yield of 40%. The work is highlighted by a novel one-pot transformation from isoxazolidin-5-one intermediate 6 to the final product, a step that can also be used to form beta-amino acids.