(2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate | 298202-10-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate
• 英文别名: [(2-methylpropan-2-yl)oxycarbonylamino] (2S,3R,4E,6E,8S,9S)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoate
• CAS: 298202-10-5
• 化学式: C₂₅H₃₇NO₆
• 分子量: 447.572
• InChiKey: MRUZOAWBWJVNRM-BMGFNHCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate 在 samarium diiodide 、 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 (2S,3S,8S,9S)-N-Boc Adda
  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：

  (2E,4E,6S,7S)-7-methoxy-4,6-dimethyl-8-phenyl-2,4-octadienal 在 三氟甲磺酸二丁硼 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.08h， 生成 (2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate
  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

• Facile and rapid access to linear and truncated microcystin analogues for the implementation of immunoassays
  作者：G. Clavé、C. Ronco、H. Boutal、N. Kreich、H. Volland、X. Franck、A. Romieu、P.-Y. Renard

  DOI：10.1039/b920193a

  日期：——

  microcystin-LR analogues based on Adda [(2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldecadienoic acid] or its corresponding aldol precursor linked to a polypeptide moiety have been synthesised and assessed for their binding affinity by the monoclonal antibody mAb MC159, an anti-microcystin-LR mAb recently selected by us for the detection of microcystins through various immunoassay formats

  一系列简化 微囊藻毒素 基于Adda的类似物[（2 S，3 S，8 S，9 S，4 E，6 E）-3-氨基-9-甲氧基-2,6,8-三甲基-10-苯基癸二烯酸]或其连接至多肽部分的相应的羟醛前体已被合成并通过单克隆抗体评估其结合亲和力 单抗 MC159，抗微囊藻毒素-LR 单抗我们最近选择了通过各种免疫测定形式检测微囊藻毒素的方法。由Pearson等人开发的对N -Boc-Adda的对映体特异性合成已进行了一些修饰。（有机化学快报。，2000，2，2901）这使我们能够访问以经济和省时的方式MC-LR的线性类似物小型图书馆。作为示例，选择了Adda来合成由此衍生的荧光探针β-氨基酸。随后通过肟连接将该探针固相固定，以产生适于通过SPIT-FRI方法检测微囊藻毒素的生物芯片。
• 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.