| 123719-17-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 123719-17-5
• 化学式: C₆₃H₁₁₃NO₁₃Si₂
• 分子量: 1148.76
• InChiKey: QWXMXFAPRZCQJJ-WPGGUNARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.65
• 重原子数：
  79.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  176.59
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 生成 methyl (4R,6S,7R,8S,10S,12E,14R,17S,18R,19S,22S)-3,7,17-trihydroxy-19-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-6,8-dimethoxy-4,10,12,18-tetramethyl-2,15,21-trioxo-14-prop-2-enyl-20-oxa-1-azabicyclo[20.4.0]hexacos-12-ene-3-carboxylate
  参考文献：
  名称：

  On the remarkable propensity for carbon-carbon bond cleavage reactions in the C(8)-C(10) region of FK-506

  摘要：

  It has been deduced from a series of transformations that formation of a tetrahedral intermediate at C-9 in FD-506 occasions fragmentation of the C-9-C-10 bond by a retro-Claisen-like pathway or the C-9-C-8 bond by a benzilic acid type rearrangement. Reduction of FK-506 with L-Selectride leads to the formation of a boronate ester 18 rather than to the corresponding diol 17, which had previously been formulated. Direct reduction of FK-506 with sodium triacetoxyborohydride (or hydrolysis of 18) does provide access to (22S)-dihydro FK-506 17. The former reduction also leads to some 22R epimer, which is an intermediate in the total synthesis of FK-506.

  DOI：

  10.1021/jo00008a055