(3R,4S,5S,7R,11R,12R)-12-ethyl-3,5,7,11-tetramethyl-4-[[(2S,6R)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-oxacyclododecane-2,8-dione | 1255940-50-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (3R,4S,5S,7R,11R,12R)-12-ethyl-3,5,7,11-tetramethyl-4-[[(2S,6R)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-oxacyclododecane-2,8-dione
• CAS: 1255940-50-1
• 化学式: C₂₃H₃₆O₆
• 分子量: 408.535
• InChiKey: CNIFNURAJJZMON-OPTANORISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,7R,11R,12R)-12-ethyl-3,5,7,11-tetramethyl-4-[[(2S,6R)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-oxacyclododecane-2,8-dione 在 sodium tetrahydroborate 、 水 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 乙醚 为溶剂， 反应 3.0h， 以83%的产率得到(3R,4S,5S,7R,11R,12R)-12-ethyl-4-[[(2R,3S,6S)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]oxy]-3,5,7,11-tetramethyl-oxacyclododecane-2,8-dione
  参考文献：
  名称：

  A De Novo Approach to the Synthesis of Glycosylated Methymycin Analogues with Structural and Stereochemical Diversity

  摘要：

  A divergent and highly stereoselective route to 11 glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and postglycosylation transformation. This unique application of Pd-catalyzed glycosylation demonstrates the breath of alpha/beta- and D/L-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.

  DOI：

  10.1021/ol102144g
• 作为产物：
  描述：

  tert-butyl ((2R,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate 、 8,9-dihydro-10-deoxymethynolide 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以85%的产率得到(3R,4S,5S,7R,11R,12R)-12-ethyl-3,5,7,11-tetramethyl-4-[[(2S,6R)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-oxacyclododecane-2,8-dione
  参考文献：
  名称：

  A De Novo Approach to the Synthesis of Glycosylated Methymycin Analogues with Structural and Stereochemical Diversity

  摘要：

  A divergent and highly stereoselective route to 11 glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and postglycosylation transformation. This unique application of Pd-catalyzed glycosylation demonstrates the breath of alpha/beta- and D/L-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.

  DOI：

  10.1021/ol102144g

文献信息

• A De Novo Approach to the Synthesis of Glycosylated Methymycin Analogues with Structural and Stereochemical Diversity
  作者：Svetlana A. Borisova、Sanjeeva R. Guppi、Hak Joong Kim、Bulan Wu、John H. Penn、Hung-wen Liu、George A. O’Doherty

  DOI：10.1021/ol102144g

  日期：2010.11.19

  A divergent and highly stereoselective route to 11 glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and postglycosylation transformation. This unique application of Pd-catalyzed glycosylation demonstrates the breath of alpha/beta- and D/L-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.