(2R,3R,4S,5R,6S)-2-(azidomethyl)-4,5-dimethoxy-3-pent-4-enoxy-6-phenylsulfanyloxane | 511274-68-3

• 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)-2-(azidomethyl)-4,5-dimethoxy-3-pent-4-enoxy-6-phenylsulfanyloxane
• CAS: 511274-68-3
• 化学式: C₁₉H₂₇N₃O₄S
• 分子量: 393.507
• InChiKey: VYHGSHHEKNYTHN-FQBWVUSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-2-(azidomethyl)-4,5-dimethoxy-3-pent-4-enoxy-6-phenylsulfanyloxane 在 吡啶 、 4-二甲氨基吡啶 、 Grubbs catalyst first generation 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 68.33h， 生成 (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 sodium azide 、 15-冠醚-5 、 D(+)-10-樟脑磺酸 、 四丁基碘化铵 、 sodium hydride 、 三乙胺 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 144.0h， 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

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.