Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-hydroxy-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester | 870537-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-hydroxy-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester
• 英文别名: [(2R,3R,4S,5R,6S)-3-hydroxy-4,5-dimethoxy-6-phenylsulfanyloxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 870537-88-5
• 化学式: C₂₁H₂₆O₇S₂
• 分子量: 454.565
• InChiKey: WMUPOYFNJUPNJN-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-hydroxy-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 在 sodium azide 、 15-冠醚-5 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 (2R,3R,4S,5R,6S)-2-(azidomethyl)-4,5-dimethoxy-3-pent-4-enoxy-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
• 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 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-hydroxy-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl 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.