acetyl 6-O-benzoyl-3,4-di-O-isopropylidene-2-deoxy-2-iodo-β-D-galactoside | 548460-00-0

• 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: acetyl 6-O-benzoyl-3,4-di-O-isopropylidene-2-deoxy-2-iodo-β-D-galactoside
• 英文别名: [(3aS,4R,6S,7R,7aS)-6-acetyloxy-7-iodo-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate
• CAS: 548460-00-0
• 化学式: C₁₈H₂₁IO₇
• 分子量: 476.265
• InChiKey: RGBIEUYWIBXJHT-OWVAZHOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  acetyl 6-O-benzoyl-3,4-di-O-isopropylidene-2-deoxy-2-iodo-β-D-galactoside 、 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 4,6-benzylidene-2-O-benzoyl-3-O-(6-O-benzoyl-3,4-di-O-isopropylidene-2-deoxy-2-iodo-β-D-galactopyranosyl)-(1->3)-α-D-glucopyranoside 、 methyl 4,6-benzylidene-2-O-benzoyl-3-O-(6-O-benzoyl-3,4-di-O-isopropylidene-2-deoxy-2-iodo-α-D-galactopyranosyl)-(1->3)-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of 2-Deoxy-β-Galactosides via 2-Deoxy-2-bromo- and 2-Deoxy-2-iodo-galactopyranosyl Donors

  摘要：

  A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors.

  DOI：

  10.1021/ol034393t
• 作为产物：
  描述：

  溶剂黄146 、 6-O-benzoyl-3,4-di-O-isopropylidene-D-galactal 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 acetyl 6-O-benzoyl-3,4-di-O-isopropylidene-2-deoxy-2-iodo-β-D-galactoside 、 acetyl 6-O-benzoyl-3,4-di-O-isopropylidene-2-deoxy-2-iodo-α-D-galactoside
  参考文献：
  名称：

  Stereoselective Synthesis of 2-Deoxy-β-Galactosides via 2-Deoxy-2-bromo- and 2-Deoxy-2-iodo-galactopyranosyl Donors

  摘要：

  A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors.

  DOI：

  10.1021/ol034393t