[(1E,3S,4R,5S,8R,9E,12S,14S)-5-hydroxy-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-14-methoxy-14-[(2R,3S,5R)-3-methoxy-5-methyl-6-oxooxan-2-yl]-2,4,10,12-tetramethyl-7-oxo-8-prop-2-enyltetradeca-1,9-dien-3-yl] (2S)-1-(2-methoxy-2-oxoacetyl)piperidine-2-carboxylate | 124125-40-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1E,3S,4R,5S,8R,9E,12S,14S)-5-hydroxy-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-14-methoxy-14-[(2R,3S,5R)-3-methoxy-5-methyl-6-oxooxan-2-yl]-2,4,10,12-tetramethyl-7-oxo-8-prop-2-enyltetradeca-1,9-dien-3-yl] (2S)-1-(2-methoxy-2-oxoacetyl)piperidine-2-carboxylate
• CAS: 124125-40-2
• 化学式: C₄₅H₇₁NO₁₃
• 分子量: 834.058
• InChiKey: AZZIXQQKDZMUJM-SRMNAXGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  59.0
• 可旋转键数：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  184.43
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  [(1E,3S,4R,5S,8R,9E,12S,14S)-5-hydroxy-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-14-methoxy-14-[(2R,3S,5R)-3-methoxy-5-methyl-6-oxooxan-2-yl]-2,4,10,12-tetramethyl-7-oxo-8-prop-2-enyltetradeca-1,9-dien-3-yl] (2S)-1-(2-methoxy-2-oxoacetyl)piperidine-2-carboxylate 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Coleman, Robert S.; Danishefsky, Samuel J., Heterocycles, 1989, vol. 28, # 1, p. 157 - 161

  摘要：

  DOI：
• 作为产物：
  描述：

  他克莫司 在 lead(IV) acetate 、 potassium cyanide 、 18-冠醚-6 作用下， 以 苯 为溶剂， 反应 20.5h， 生成 [(1E,3S,4R,5S,8R,9E,12S,14S)-5-hydroxy-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-14-methoxy-14-[(2R,3S,5R)-3-methoxy-5-methyl-6-oxooxan-2-yl]-2,4,10,12-tetramethyl-7-oxo-8-prop-2-enyltetradeca-1,9-dien-3-yl] (2S)-1-(2-methoxy-2-oxoacetyl)piperidine-2-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

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：——