(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-N-benzyl-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-azacyclopentadecane-6-carbothioamide | 166036-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-N-benzyl-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-azacyclopentadecane-6-carbothioamide
• CAS: 166036-09-5
• 化学式: C₄₅H₇₇N₃O₁₂S
• 分子量: 884.185
• InChiKey: YDPIZHSCGMSHNJ-GJLLBZPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  61
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  224
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-N-benzyl-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-azacyclopentadecane-6-carbothioamide 在 solid phase supported N-methyl-2-chloropyridinium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 9a,11-O-(N'-benzylcarbonimidoyl)-3-decladinosyl-9-deoxo-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Novel 9a,11-bridged azalides: One-pot synthesis of N′-substituted 2-imino-1,3-oxazolidines condensed to an azalide aglycone

  摘要：

  An efficient one-pot method for the synthesis of novel 9a,11-bridged 15-membered 9a-aza-9-deoxo-9a-homoerythromycin A and its 6-O-methyl analogue has been developed. The novel bicyclic azalide scaffold is characterized by an N'-substituted-2-imino-1,3-oxazolidine moiety bound to a macrolactone ring between positions 9a and 11. Removal of the cladinose sugar from the starting compounds allows easy preparation of a small series of such bicyclic 3-keto and 3,6-hemiketal azalide derivatives. A mechanism for the formation of N'-substituted-2-imino-1,3-oxazolidines is discussed. Antibacterial properties of the prepared compounds were evaluated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.061
• 作为产物：
  描述：

  异硫氰酸苯甲酯 、 阿奇霉素 A 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以92%的产率得到(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-N-benzyl-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-azacyclopentadecane-6-carbothioamide
  参考文献：
  名称：

  Novel 9a,11-bridged azalides: One-pot synthesis of N′-substituted 2-imino-1,3-oxazolidines condensed to an azalide aglycone

  摘要：

  An efficient one-pot method for the synthesis of novel 9a,11-bridged 15-membered 9a-aza-9-deoxo-9a-homoerythromycin A and its 6-O-methyl analogue has been developed. The novel bicyclic azalide scaffold is characterized by an N'-substituted-2-imino-1,3-oxazolidine moiety bound to a macrolactone ring between positions 9a and 11. Removal of the cladinose sugar from the starting compounds allows easy preparation of a small series of such bicyclic 3-keto and 3,6-hemiketal azalide derivatives. A mechanism for the formation of N'-substituted-2-imino-1,3-oxazolidines is discussed. Antibacterial properties of the prepared compounds were evaluated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.061

文献信息

• 9A-Carbamoyl and Thiocarbamoyl Azalides With Antimalarial Activity
  申请人：Mutak Stjepan

  公开号：US20080227730A1

  公开（公告）日：2008-09-18

  9a-carbamoyl and thiocarbamoyl azalides A and their pharmaceutically acceptable derivatives are useful for treatment and prevention of malaria.
• Novel 9a,11-bridged azalides: One-pot synthesis of N′-substituted 2-imino-1,3-oxazolidines condensed to an azalide aglycone
  作者：Zorica Marušić Ištuk、Ana Čikoš、Dubravka Gembarovski、Gorjana Lazarevski、Ivica Đilović、Dubravka Matković-Čalogović、Goran Kragol

  DOI：10.1016/j.bmc.2010.10.061

  日期：2011.1

  An efficient one-pot method for the synthesis of novel 9a,11-bridged 15-membered 9a-aza-9-deoxo-9a-homoerythromycin A and its 6-O-methyl analogue has been developed. The novel bicyclic azalide scaffold is characterized by an N'-substituted-2-imino-1,3-oxazolidine moiety bound to a macrolactone ring between positions 9a and 11. Removal of the cladinose sugar from the starting compounds allows easy preparation of a small series of such bicyclic 3-keto and 3,6-hemiketal azalide derivatives. A mechanism for the formation of N'-substituted-2-imino-1,3-oxazolidines is discussed. Antibacterial properties of the prepared compounds were evaluated. (C) 2010 Elsevier Ltd. All rights reserved.