methyl 3-O-(2-hydroxyethyl)-4-azido-2-O-benzyl-4,6-dideoxy-α-D-glucopyranoside | 502621-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-(2-hydroxyethyl)-4-azido-2-O-benzyl-4,6-dideoxy-α-D-glucopyranoside
• CAS: 502621-12-7
• 化学式: C₁₆H₂₃N₃O₅
• 分子量: 337.376
• InChiKey: NDLQJSLCASYHRR-JZYAIQKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105.91
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 3-O-(2-hydroxyethyl)-4-azido-2-O-benzyl-4,6-dideoxy-α-D-glucopyranoside 在 硫酸 作用下， 以65%的产率得到acetyl 3-O-(2-acetoxyethyl)-4-azido-2-O-acetyl-4,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Exploring the Optimal Site for Modifications of Pyranmycins with the Extended Arm Approach

  摘要：

  [GRAPHICS]Continuing from the syntheses and the antibacterial studies of a library of pyranmycins, we further probed the proximity around ring III of pyranmycin by introducing an "extended arm" that has hydroxyethyl or aminoethyl groups at the O-2", O-3", or O-4" positions. The results from the antibacterial studies reveal the optimal structural motif is the attachment of an extended arm with a terminal hydroxyl group at the O-3" position.

  DOI：

  10.1021/ol027288c
• 作为产物：
  描述：

  (2R,4R,5R,6S)-4-Allyloxy-5-benzyloxy-6-methoxy-2-methyl-dihydro-pyran-3-one 在 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 methyl 3-O-(2-hydroxyethyl)-4-azido-2-O-benzyl-4,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Exploring the Optimal Site for Modifications of Pyranmycins with the Extended Arm Approach

  摘要：

  [GRAPHICS]Continuing from the syntheses and the antibacterial studies of a library of pyranmycins, we further probed the proximity around ring III of pyranmycin by introducing an "extended arm" that has hydroxyethyl or aminoethyl groups at the O-2", O-3", or O-4" positions. The results from the antibacterial studies reveal the optimal structural motif is the attachment of an extended arm with a terminal hydroxyl group at the O-3" position.

  DOI：

  10.1021/ol027288c