Undec-10-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-undec-10-enoyloxymethyl-tetrahydro-pyran-3-yl ester | 511274-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Undec-10-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-undec-10-enoyloxymethyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-3-undec-10-enoyloxyoxan-2-yl]methyl undec-10-enoate
• CAS: 511274-76-3
• 化学式: C₃₇H₅₈O₇
• 分子量: 614.863
• InChiKey: FELRQGWMEQVJSM-ACKRORFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  44
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  Undec-10-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-undec-10-enoyloxymethyl-tetrahydro-pyran-3-yl ester 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以43%的产率得到(E)-(2S,3S,4R,4aR,27aR)-2-Benzyl-3,4-dimethoxy-2,3,4,4a,7,8,9,10,11,12,13,14,17,18,19,20,21,22,23,24,27,27a-docosahydro-1,5,26-trioxa-benzocyclopentacosene-6,25-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,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 D(+)-10-樟脑磺酸 、 氢气 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 110.0 ℃ 、405.3 kPa 条件下， 反应 63.0h， 生成 Undec-10-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-undec-10-enoyloxymethyl-tetrahydro-pyran-3-yl ester
  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.