[(2R,3R,4R,5S,6S)-3-hept-6-enoyloxy-4,5-dimethoxy-6-phenyloxan-2-yl]methyl hept-6-enoate | 511274-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5S,6S)-3-hept-6-enoyloxy-4,5-dimethoxy-6-phenyloxan-2-yl]methyl hept-6-enoate
• CAS: 511274-75-2
• 化学式: C₂₈H₄₀O₇
• 分子量: 488.621
• InChiKey: FZQMRQGCTBKZKO-LSNQXMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5S,6S)-3-hept-6-enoyloxy-4,5-dimethoxy-6-phenyloxan-2-yl]methyl hept-6-enoate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 46.0h， 以60%的产率得到(E)-(2S,3S,4R,4aR,19aR)-3,4-Dimethoxy-2-phenyl-2,3,4,4a,7,8,9,10,13,14,15,16,19,19a-tetradecahydro-1,5,18-trioxa-benzocycloheptadecene-6,17-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
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene 在 吡啶 、 4-二甲氨基吡啶 、 D(+)-10-樟脑磺酸 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 [(2R,3R,4R,5S,6S)-3-hept-6-enoyloxy-4,5-dimethoxy-6-phenyloxan-2-yl]methyl hept-6-enoate
  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.