(1S,3R,5S,6S,7S,8S)-1'-{2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl}-(1''→1')-{1-O-((1'S,3'R,5'R,6'S,7'S,8'S)-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]octane | 1397285-65-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,3R,5S,6S,7S,8S)-1'-{2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl}-(1''→1')-{1-O-((1'S,3'R,5'R,6'S,7'S,8'S)-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]octane
• CAS: 1397285-65-2
• 化学式: C₉₁H₈₆O₂₀
• 分子量: 1499.67
• InChiKey: RGJLMHUKFOJGOG-SKZBIVLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.17
• 重原子数：
  111.0
• 可旋转键数：
  32.0
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  215.96
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,5S,6S,7S,8S)-1'-{2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl}-(1''→1')-{1-O-((1'S,3'R,5'R,6'S,7'S,8'S)-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]octane 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以82%的产率得到(1S,3R,5S,6S,7S,8S)-1'-{β-D-glucopyranosyl}-(1''→1')-{1-O-((1'S,3'R,5'R,6'S,7'S,8'S)-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]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-{(1'S,3'R,5'R,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 、 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 以55%的产率得到(1S,3R,5S,6S,7S,8S)-1'-{2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl}-(1''→1')-{1-O-((1'S,3'R,5'R,6'S,7'S,8'S)-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]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