[(2R,3R,4S,5R,6S)-3-pent-4-enoyloxy-4,5-bis(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methyl pent-4-enoate | 511274-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5R,6S)-3-pent-4-enoyloxy-4,5-bis(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methyl pent-4-enoate
• CAS: 511274-61-6
• 化学式: C₃₆H₄₀O₇S
• 分子量: 616.775
• InChiKey: VRQDRNZRPWXSDC-ZEUWXZDFSA-N

物化性质

• 沸点：
  680.5±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6S)-3-pent-4-enoyloxy-4,5-bis(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methyl pent-4-enoate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 95.0h， 以70%的产率得到(1R,6E,13R,15S,16R,17S)-16,17-bis(phenylmethoxy)-15-phenylsulfanyl-2,11,14-trioxabicyclo[11.4.0]heptadec-6-ene-3,10-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：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 4-二甲氨基吡啶 、 D(+)-10-樟脑磺酸 、 sodium hydride 、 potassium carbonate 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 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 270.0h， 生成 [(2R,3R,4S,5R,6S)-3-pent-4-enoyloxy-4,5-bis(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methyl pent-4-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.