6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose | 263916-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose
• 英文别名: [(2R)-2-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethyl] acetate
• CAS: 263916-91-2
• 化学式: C₂₇H₃₄O₁₀S
• 分子量: 550.627
• InChiKey: SWMNUMHZUHCYND-WSGIOKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose 在 palladium on activated charcoal 氢气 、 三氟乙酸 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 5-O-(β-iodoethyl)-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of 5-O-β-Iodoethyl-D-Glucofuranose

  摘要：

  The preparation of an iodinated derivative of D-glucose where a beta-iodoethyl moiety has been introduced at O-5 is presented. In such an analogue the existence of pyranose forms is precluded and the iodinated tag Lies in a region of the carbohydrate not judged essential for recognition by the glucose transport protein; also noteworthy in such a compound is the stability of the carbon-iodine bond, a prerequisite for its potential use in SPECT medical imaging.

  DOI：

  10.1080/07328300008544068
• 作为产物：
  描述：

  6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(prop-2'-enyl)-α-D-glucofuranose 在 臭氧 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of 5-O-β-Iodoethyl-D-Glucofuranose

  摘要：

  The preparation of an iodinated derivative of D-glucose where a beta-iodoethyl moiety has been introduced at O-5 is presented. In such an analogue the existence of pyranose forms is precluded and the iodinated tag Lies in a region of the carbohydrate not judged essential for recognition by the glucose transport protein; also noteworthy in such a compound is the stability of the carbon-iodine bond, a prerequisite for its potential use in SPECT medical imaging.

  DOI：

  10.1080/07328300008544068