(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 | 1397285-63-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 1397285-63-0
• 化学式: C₆₃H₇₀O₁₆
• 分子量: 1083.24
• InChiKey: BZTJWBWCCNKDMJ-BQSQJFAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  79.0
• 可旋转键数：
  24.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  191.68
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (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 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 以96%的产率得到(1S,3R,5S,6S,7S,8S)-1'-{β-D-glucopyranosyl}-(1''→1')-{1-O-((1'S,3'R,5'S,6'S,7'S,8'S)-4'-oxaspiro[2.5]octan-6',7',8'-triol-5'-yl)}-(5'→1)-6,7,8-tri-O-benzyl-5-O-methyl-4-oxaspiro[2.5]octan-6,7,8-triol
  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'-{2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl}-(1''→1')-{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-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67%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