Pent-4-enoic acid ((2R,3R,4S,5R,6S)-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amide | 870537-93-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Pent-4-enoic acid ((2R,3R,4S,5R,6S)-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amide
• 英文别名: N-[[(2R,3R,4S,5R,6S)-4,5-dimethoxy-3-pent-4-enoxy-6-phenylsulfanyloxan-2-yl]methyl]pent-4-enamide
• CAS: 870537-93-2
• 化学式: C₂₄H₃₅NO₅S
• 分子量: 449.612
• InChiKey: SZUXJIJWQAQFJE-ZXGKGEBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Pent-4-enoic acid ((2R,3R,4S,5R,6S)-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amide 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以19%的产率得到(E)-(2S,3R,4S,4aR,15aR)-3,4-Dimethoxy-2-phenylsulfanyl-3,4,4a,7,8,11,12,14,15,15a-decahydro-2H,6H-1,5-dioxa-14-aza-benzocyclotridecen-13-one
  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 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 15-冠醚-5 、 D(+)-10-樟脑磺酸 、 水 、 四丁基碘化铵 、 sodium hydride 、 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 194.33h， 生成 Pent-4-enoic acid ((2R,3R,4S,5R,6S)-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amide
  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

• US7534871B2
  申请人：——

  公开号：US7534871B2

  公开（公告）日：2009-05-19
• 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.