methyl (2R,4S,5R,6S,8S,10E,12R)-12-[(4S,5R,6S)-2,4-dihydroxy-6-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-5-methyloxan-2-yl]-5-hydroxy-4,6-dimethoxy-2,8,10-trimethylpentadeca-10,14-dienoate | 133548-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,4S,5R,6S,8S,10E,12R)-12-[(4S,5R,6S)-2,4-dihydroxy-6-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-5-methyloxan-2-yl]-5-hydroxy-4,6-dimethoxy-2,8,10-trimethylpentadeca-10,14-dienoate
• CAS: 133548-78-4
• 化学式: C₃₇H₆₄O₁₀
• 分子量: 668.909
• InChiKey: GDJQLLCWCBFTQC-FIEFOTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  47.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  144.14
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl (2R,4S,5R,6S,8S,10E,12R,15S,17S,18E)-5,15,17-trihydroxy-19-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-4,6-dimethoxy-2,8,10,16,18-pentamethyl-13-oxo-12-prop-2-enylnonadeca-10,18-dienoate 、 methyl (2R,4S,5R,6S,8S,10E,12R)-12-[(4S,5R,6S)-2,4-dihydroxy-6-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-5-methyloxan-2-yl]-5-hydroxy-4,6-dimethoxy-2,8,10-trimethylpentadeca-10,14-dienoate 、 硼氢化钠 、 甲醇 生成 methyl (2R,4S,5R,6S,8S,10E,12R,13S,15S,17S,18E)-5,13,15,17-tetrahydroxy-19-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-4,6-dimethoxy-2,8,10,16,18-pentamethyl-12-prop-2-enylnonadeca-10,18-dienoate
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  他克莫司 、 苄胺 、 氰基硼氢化钠 、 甲醇 生成 methyl (2R,4S,5R,6S,8S,10E,12R)-12-[(4S,5R,6S)-2,4-dihydroxy-6-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-5-methyloxan-2-yl]-5-hydroxy-4,6-dimethoxy-2,8,10-trimethylpentadeca-10,14-dienoate
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• On the remarkable propensity for carbon-carbon bond cleavage reactions in the C(8)-C(10) region of FK-506
  作者：Matthew J. Fisher、Ken Chow、Anabella Villalobos、Samuel J. Danishefsky

  DOI：10.1021/jo00008a055

  日期：1991.4

  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.