(E)-5-{(5aR,6R,7aS,11R,12aS,12bR)-11-[(E)-(S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-2,2,4,4-tetraisopropyl-5a,7a,8,11,12a,12b-hexahydro-6H-1,3,5,7,12-pentaoxa-2,4-disila-benzo[1,2;3,4]dicyclohepten-6-yl}-pent-2-enoic acid methyl ester | 365569-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-{(5aR,6R,7aS,11R,12aS,12bR)-11-[(E)-(S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-2,2,4,4-tetraisopropyl-5a,7a,8,11,12a,12b-hexahydro-6H-1,3,5,7,12-pentaoxa-2,4-disila-benzo[1,2;3,4]dicyclohepten-6-yl}-pent-2-enoic acid methyl ester
• CAS: 365569-84-2
• 化学式: C₄₃H₈₂O₉Si₄
• 分子量: 855.461
• InChiKey: PINKSXUTXIWNIQ-GQBLIJTKSA-N

反应信息

• 作为反应物：
  描述：

  (E)-5-{(5aR,6R,7aS,11R,12aS,12bR)-11-[(E)-(S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-2,2,4,4-tetraisopropyl-5a,7a,8,11,12a,12b-hexahydro-6H-1,3,5,7,12-pentaoxa-2,4-disila-benzo[1,2;3,4]dicyclohepten-6-yl}-pent-2-enoic acid methyl ester 在 四丁基氟化铵 、 吡啶 、 乙酸酐 、 lithium hydroxide 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 [(2S,4aR,5aS,9R,10aR,11S,11aS)-9-((E)-(S)-3,4-Dihydroxy-but-1-enyl)-11-hydroxy-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-acetic acid
  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：

  3-{(5aR,6R,7aS,11R,12aS,12bR)-11-[(E)-(S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-2,2,4,4-tetraisopropyl-5a,7a,8,11,12a,12b-hexahydro-6H-1,3,5,7,12-pentaoxa-2,4-disila-benzo[1,2;3,4]dicyclohepten-6-yl}-propan-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-5-{(5aR,6R,7aS,11R,12aS,12bR)-11-[(E)-(S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-2,2,4,4-tetraisopropyl-5a,7a,8,11,12a,12b-hexahydro-6H-1,3,5,7,12-pentaoxa-2,4-disila-benzo[1,2;3,4]dicyclohepten-6-yl}-pent-2-enoic acid methyl 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