(1S,3R,5S,6S,7S,8S)-1-O-{(1'S,3'R,5'S,6'S,7'S,8'S)-1'-O-acetyl-6',7',8'-tri-O-benzyl-4'-oxaspiro[2.5]octan-5'-yl}-(5'→1)-6,7,8-tri-O-benzyl-5-O-methyl-4-oxaspiro[2.5]octan | 1397285-47-0

• 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: (1S,3R,5S,6S,7S,8S)-1-O-{(1'S,3'R,5'S,6'S,7'S,8'S)-1'-O-acetyl-6',7',8'-tri-O-benzyl-4'-oxaspiro[2.5]octan-5'-yl}-(5'→1)-6,7,8-tri-O-benzyl-5-O-methyl-4-oxaspiro[2.5]octan
• CAS: 1397285-47-0
• 化学式: C₅₉H₆₂O₁₂
• 分子量: 963.134
• InChiKey: DACDSMFPAQMWLE-BJBMLHNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.46
• 重原子数：
  71.0
• 可旋转键数：
  22.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  118.6
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,5S,6S,7S,8S)-1-O-{(1'S,3'R,5'S,6'S,7'S,8'S)-1'-O-acetyl-6',7',8'-tri-O-benzyl-4'-oxaspiro[2.5]octan-5'-yl}-(5'→1)-6,7,8-tri-O-benzyl-5-O-methyl-4-oxaspiro[2.5]octan 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以50%的产率得到(1S,3R,5S,6S,7S,8S)-1-O-{(1'S,3'R,5'S,6'S,7'S,8'S)-6',7',8'-tri-O-benzyl-4'-oxaspiro[2.5]octan-1'-ol-5'-yl}-(5'→1)-6,7,8-tri-O-benzyl-5-O-methyl-4-oxaspiro[2.5]octane
  参考文献：
  名称：

  Glycosylations of Cyclopropyl-Modified Carbohydrates: Remarkable β-Selectivity Using a Mannose Building Block

  摘要：

  A mannosyl donor bearing a spiroannulated cyclopropane unit at C-5 has been prepared, and its behavior in glycosylation reactions investigated. Selectivities in favor of the beta-anomer were observed. Corresponding di- and trisaccharides incorporating the rigid cyclopropane motif were assembled.

  DOI：

  10.1021/ol3024133
• 作为产物：
  描述：

  (1S,3R,5S,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-O-pmethoxyphenyl-4-oxaspiro[2.5]octane 在 ammonium cerium (IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 (1S,3R,5S,6S,7S,8S)-1-O-{(1'S,3'R,5'S,6'S,7'S,8'S)-1'-O-acetyl-6',7',8'-tri-O-benzyl-4'-oxaspiro[2.5]octan-5'-yl}-(5'→1)-6,7,8-tri-O-benzyl-5-O-methyl-4-oxaspiro[2.5]octan
  参考文献：
  名称：

  Glycosylations of Cyclopropyl-Modified Carbohydrates: Remarkable β-Selectivity Using a Mannose Building Block

  摘要：

  A mannosyl donor bearing a spiroannulated cyclopropane unit at C-5 has been prepared, and its behavior in glycosylation reactions investigated. Selectivities in favor of the beta-anomer were observed. Corresponding di- and trisaccharides incorporating the rigid cyclopropane motif were assembled.

  DOI：

  10.1021/ol3024133