(E)-3-[(2R,3R,4R,4aS,9aS)-4-Benzyloxy-2-(2-oxo-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-acrylic acid ethyl ester | 365569-88-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-[(2R,3R,4R,4aS,9aS)-4-Benzyloxy-2-(2-oxo-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-acrylic acid ethyl ester
• CAS: 365569-88-6
• 化学式: C₂₃H₂₈O₇
• 分子量: 416.471
• InChiKey: HZJIGPFOFMBUKF-RVOPKCIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (E)-3-[(2R,3R,4R,4aS,9aS)-4-Benzyloxy-2-(2-oxo-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-acrylic acid ethyl ester 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到((2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-hydroxy-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Concise Synthesis of Ciguatoxin ABC-Ring Fragments and Surface Plasmon Resonance Study of the Interaction of their BSA Conjugates with Monoclonal Antibodies

  摘要：

  Monoclonal antibodies (mAbs), 4H2 and 6H7, were prepared previously using a protein conjugate of a 1:1 epimeric mixture of the synthetic ABC-ring fragments or ciguatoxin (CTX), 3 and 4. Here, the interactions of these mAbs with the fragments of CTX and CTX3C, 3 and 5, were investigated by surface plasmon resonance (SPR) spectroscopy in an attempt to clarify an antigenic determinant. Compared with the previous synthesis, the fragment 3 possessing the 2S configuration was synthesized from tri-O-acetyl-D-glucal much more effectively. The mAb 4H2 was already known to show a dose-dependent binding to the bovine serum albumin (BSA) conjugate of 3, bur not to that of 5. The present SPR study of 4H2 demonstrates that the A-ring side chain of 3 plays a decisive role as an epitope. Therefore, SPR can effectively replace the ELISA method for the analysis of mAbs. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00358-4
• 作为产物：
  描述：

  (2R,3R,4S,4aS,9aS)-4-Benzyloxy-2-[1,3]dithian-2-ylmethyl-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-ol 在 N-甲基吗啉 、 碳酸氢钠 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (E)-3-[(2R,3R,4R,4aS,9aS)-4-Benzyloxy-2-(2-oxo-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-acrylic acid ethyl ester
  参考文献：
  名称：

  Concise Synthesis of Ciguatoxin ABC-Ring Fragments and Surface Plasmon Resonance Study of the Interaction of their BSA Conjugates with Monoclonal Antibodies

  摘要：

  Monoclonal antibodies (mAbs), 4H2 and 6H7, were prepared previously using a protein conjugate of a 1:1 epimeric mixture of the synthetic ABC-ring fragments or ciguatoxin (CTX), 3 and 4. Here, the interactions of these mAbs with the fragments of CTX and CTX3C, 3 and 5, were investigated by surface plasmon resonance (SPR) spectroscopy in an attempt to clarify an antigenic determinant. Compared with the previous synthesis, the fragment 3 possessing the 2S configuration was synthesized from tri-O-acetyl-D-glucal much more effectively. The mAb 4H2 was already known to show a dose-dependent binding to the bovine serum albumin (BSA) conjugate of 3, bur not to that of 5. The present SPR study of 4H2 demonstrates that the A-ring side chain of 3 plays a decisive role as an epitope. Therefore, SPR can effectively replace the ELISA method for the analysis of mAbs. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00358-4