{(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'→4)-methyl 2,3,6-tri-O-benzyl-a-D-glucoside | 1397285-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(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'→4)-methyl 2,3,6-tri-O-benzyl-a-D-glucoside
• CAS: 1397285-53-8
• 化学式: C₅₈H₆₂O₁₂
• 分子量: 951.123
• InChiKey: PKFPVUMPFJBNOP-SNJVCVCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.32
• 重原子数：
  70.0
• 可旋转键数：
  23.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  118.6
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  (1S,3R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-4-oxaspiro[2.5]octan-5-ol 在 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 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 {(1'S,3'R,5'R,6'S,7'S,8'S)-1'-O-acetyl-6',7',8'-tri-O-benzyl-4'-oxaspiro[2.5]octan-5'-yl}-(5'→4)-methyl 2,3,6-tri-O-benzyl-a-D-glucoside 、 {(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'→4)-methyl 2,3,6-tri-O-benzyl-a-D-glucoside
  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