(2R,3R,4S,5R,6S)-4,5-dimethoxy-3-pent-4-enoxy-2-(pent-4-enoxymethyl)-6-phenylsulfanyloxane | 870537-92-1

• 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)-4,5-dimethoxy-3-pent-4-enoxy-2-(pent-4-enoxymethyl)-6-phenylsulfanyloxane
• CAS: 870537-92-1
• 化学式: C₂₄H₃₆O₅S
• 分子量: 436.613
• InChiKey: JKPSAKCSFVAHPX-SJSRKZJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-4,5-dimethoxy-3-pent-4-enoxy-2-(pent-4-enoxymethyl)-6-phenylsulfanyloxane 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 95.0h， 生成 (Z)-(3S,4R,4aR,11aR)-3,4-Dimethoxy-2,3,4,4a,6,9,11,11a-octahydro-1,5,10-trioxa-benzocyclononene
  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：

  phenyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-β-D-glucopyranose 在 D(+)-10-樟脑磺酸 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 90.0h， 生成 (2R,3R,4S,5R,6S)-4,5-dimethoxy-3-pent-4-enoxy-2-(pent-4-enoxymethyl)-6-phenylsulfanyloxane
  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.