X-206-benzyl ester-22-phenylthionocarbonate | 247137-59-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: X-206-benzyl ester-22-phenylthionocarbonate
• 英文别名: benzyl (2R)-2-[(2S,3S,6R)-6-[(2R,3S)-3-[(2R,5S,6R)-6-[[(2R,3S,5R,6R)-6-[(R)-[(2S,5S)-5-[(2R,3R,5S)-5-[(2R,5R,6S)-6-ethyl-5-hydroxy-5-methyloxan-2-yl]-2-hydroxy-3,5-dimethyloxolan-2-yl]-5-methyloxolan-2-yl]-phenoxycarbothioyloxymethyl]-6-hydroxy-3,5-dimethyloxan-2-yl]methyl]-6-hydroxy-5-methyloxan-2-yl]-2-hydroxybutyl]-3-methyloxan-2-yl]propanoate
• CAS: 247137-59-3
• 化学式: C₆₁H₉₂O₁₅S
• 分子量: 1097.46
• InChiKey: AQBDNTODAPGWKH-HLPRAAPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  77
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  233
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  X-206-benzyl ester-22-phenylthionocarbonate 在 三(三甲基硅基)硅烷 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以75%的产率得到22-desoxy-X-206-benzyl ester
  参考文献：
  名称：

  Use of the Potassium Ion as a Template for the Selective Derivatization of the Antibiotic X-206

  摘要：

  The templating effect of potassium ions on the ionophore antibiotic X-206 (1) ensured that most of the hydroxy, hemiacetal, and ether groups were involved in encapsulation of the metal atom, which allowed a selective derivatization at the unbound C(22) position. The mechanism of acylation at, C(22) was investigated and the aquired knowledge used to achieve selective reactions on the benzyl ester 8 using a similar metal template protection.

  DOI：

  10.1021/jo9903151
• 作为产物：
  描述：

  抗生素X206 在 吡啶 、 4-二甲氨基吡啶 、 四双(4-氯苯基)硼酸钾 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 X-206-benzyl ester-22-phenylthionocarbonate
  参考文献：
  名称：

  Use of the Potassium Ion as a Template for the Selective Derivatization of the Antibiotic X-206

  摘要：

  The templating effect of potassium ions on the ionophore antibiotic X-206 (1) ensured that most of the hydroxy, hemiacetal, and ether groups were involved in encapsulation of the metal atom, which allowed a selective derivatization at the unbound C(22) position. The mechanism of acylation at, C(22) was investigated and the aquired knowledge used to achieve selective reactions on the benzyl ester 8 using a similar metal template protection.

  DOI：

  10.1021/jo9903151

文献信息

• Use of the Potassium Ion as a Template for the Selective Derivatization of the Antibiotic X-206
  作者：Anthony C. O'Sulliva、Fritz Struber、Steven V. Ley

  DOI：10.1021/jo9903151

  日期：1999.8.1

  The templating effect of potassium ions on the ionophore antibiotic X-206 (1) ensured that most of the hydroxy, hemiacetal, and ether groups were involved in encapsulation of the metal atom, which allowed a selective derivatization at the unbound C(22) position. The mechanism of acylation at, C(22) was investigated and the aquired knowledge used to achieve selective reactions on the benzyl ester 8 using a similar metal template protection.