(E)-(2S,3R,4S,4aR,15aR)-3,4-Dimethoxy-2-phenylsulfanyl-3,4,4a,7,8,11,12,14,15,15a-decahydro-2H-1,5-dioxa-14-aza-benzocyclotridecene-6,13-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (E)-(2S,3R,4S,4aR,15aR)-3,4-Dimethoxy-2-phenylsulfanyl-3,4,4a,7,8,11,12,14,15,15a-decahydro-2H-1,5-dioxa-14-aza-benzocyclotridecene-6,13-dione
• 英文别名: (1R,13R,15S,16R,17S)-16,17-dimethoxy-15-phenylsulfanyl-2,14-dioxa-11-azabicyclo[11.4.0]heptadec-6-ene-3,10-dione
• 化学式: C₂₂H₂₉NO₆S
• 分子量: 435.541
• InChiKey: NOLVVTUAOSZXKV-OSKXVONFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-β-D-glucopyranose 在 Grubbs catalyst first generation 、 sodium azide 、 15-冠醚-5 、 D(+)-10-樟脑磺酸 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 208.0h， 生成 (E)-(2S,3R,4S,4aR,15aR)-3,4-Dimethoxy-2-phenylsulfanyl-3,4,4a,7,8,11,12,14,15,15a-decahydro-2H-1,5-dioxa-14-aza-benzocyclotridecene-6,13-dione
  参考文献：
  名称：

  A Convergent Ring-Closing Metathesis Approach to Carbohydrate-Based Macrolides with Potential Antibiotic Activity

  摘要：

  An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against, Gram-positive and Gram-negative bacteria, including resistant strains, yeasts, and molds.

  DOI：

  10.1021/jo051021k

文献信息

• A Convergent Ring-Closing Metathesis Approach to Carbohydrate-Based Macrolides with Potential Antibiotic Activity
  作者：Petra Blom、Bart Ruttens、Steven Van Hoof、Idzi Hubrecht、Johan Van der Eycken、Benedikt Sas、Johan Van hemel、Jan Vandenkerckhove

  DOI：10.1021/jo051021k

  日期：2005.11.1

  An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against, Gram-positive and Gram-negative bacteria, including resistant strains, yeasts, and molds.