(2S,3R,6R)-6-(((3R,4S,5S,7R,11R,12R)-12-ethyl-3,5,7,11-tetramethyl-2,8-dioxooxacyclododecan-4-yl)oxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl methyl carbonate | 1255940-38-5

• 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
• 英文名称: (2S,3R,6R)-6-(((3R,4S,5S,7R,11R,12R)-12-ethyl-3,5,7,11-tetramethyl-2,8-dioxooxacyclododecan-4-yl)oxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl methyl carbonate
• CAS: 1255940-38-5
• 化学式: C₂₅H₄₀O₈
• 分子量: 468.588
• InChiKey: KOVJQTAIKVCZNK-DYDXUUNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,6R)-6-(((3R,4S,5S,7R,11R,12R)-12-ethyl-3,5,7,11-tetramethyl-2,8-dioxooxacyclododecan-4-yl)oxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl methyl carbonate 在 bis(η3-allyl-μ-chloropalladium(II)) 、 叠氮基三甲基硅烷 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以85%的产率得到(3R,4S,5S,7R,11R,12R)-4-(((2R,5R,6S)-5-azido-6-methyl-5,6-dihydro-2H-pyran-2-yl)oxy)-12-ethyl-3,5,7,11-tetramethyloxacyclododecane-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：

  (3R,4S,5S,7R,11R,12R)-12-ethyl-4-(((2R,5R,6S)-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-yl)oxy)-3,5,7,11-tetramethyloxacyclododecane-2,8-dione 、 氯甲酸甲酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(2S,3R,6R)-6-(((3R,4S,5S,7R,11R,12R)-12-ethyl-3,5,7,11-tetramethyl-2,8-dioxooxacyclododecan-4-yl)oxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl methyl carbonate
  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