(1R,9S,12S,13R,14S,18S,19R,20E,23S,25S,26R,27S,29R)-16-butan-2-yl-1-hydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-25,27-dimethoxy-13,21,23,29-tetramethyl-19-prop-2-enyl-11,15,17,30-tetraoxa-4-aza-16-boratetracyclo[24.3.1.114,18.04,9]hentriacont-20-ene-2,3,10-trione | 133523-46-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯内酰胺
• 英文名称: (1R,9S,12S,13R,14S,18S,19R,20E,23S,25S,26R,27S,29R)-16-butan-2-yl-1-hydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-25,27-dimethoxy-13,21,23,29-tetramethyl-19-prop-2-enyl-11,15,17,30-tetraoxa-4-aza-16-boratetracyclo[24.3.1.114,18.04,9]hentriacont-20-ene-2,3,10-trione
• CAS: 133523-46-3
• 化学式: C₄₈H₇₈BNO₁₂
• 分子量: 871.958
• InChiKey: KXEQLKFUSVEOEN-QQEWCKTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  62.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  159.52
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (1R,9S,12S,13R,14S,18S,19R,20E,23S,25S,26R,27S,29R)-16-butan-2-yl-1-hydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-25,27-dimethoxy-13,21,23,29-tetramethyl-19-prop-2-enyl-11,15,17,30-tetraoxa-4-aza-16-boratetracyclo[24.3.1.114,18.04,9]hentriacont-20-ene-2,3,10-trione 在 水 、 sodium cyanoborohydride 、 苄胺 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成
  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

文献信息

• FISHER, MATTHEW J.;CHOW, KEN;VILLALOBOS, ANABELLA;DANISHEFSKY, SAMUEL J., J. ORG. CHEM., 56,(1991) N, C. 2900-2907
  作者：FISHER, MATTHEW J.、CHOW, KEN、VILLALOBOS, ANABELLA、DANISHEFSKY, SAMUEL J.

  DOI：——

  日期：——