(3R,4S,5S,7R,11R,12R)-4-[(2R,3R,4R,5R,6S)-5-azido-3,4-dihydroxy-6-methyloxan-2-yl]oxy-12-ethyl-3,5,7,11-tetramethyl-oxacyclododecane-2,8-dione | 1255940-44-3

• 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)-4-[(2R,3R,4R,5R,6S)-5-azido-3,4-dihydroxy-6-methyloxan-2-yl]oxy-12-ethyl-3,5,7,11-tetramethyl-oxacyclododecane-2,8-dione
• CAS: 1255940-44-3
• 化学式: C₂₃H₃₉N₃O₇
• 分子量: 469.579
• InChiKey: SKJUGYKZVZILJJ-WTPBDYFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,7R,11R,12R)-4-[(2R,3R,4R,5R,6S)-5-azido-3,4-dihydroxy-6-methyloxan-2-yl]oxy-12-ethyl-3,5,7,11-tetramethyl-oxacyclododecane-2,8-dione 在 palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、689.49 kPa 条件下， 反应 6.0h， 以90%的产率得到(3R,4S,5S,7R,11R,12R)-4-[(2R,3R,4R,5R,6S)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy-12-ethyl-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：

  (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 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到(3R,4S,5S,7R,11R,12R)-4-[(2R,3R,4R,5R,6S)-5-azido-3,4-dihydroxy-6-methyloxan-2-yl]oxy-12-ethyl-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

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.