acetyl 3,4-di-O-benzyl-2,6-dideoxy-2-iodo-α-D-galactopyranoside | 548460-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetyl 3,4-di-O-benzyl-2,6-dideoxy-2-iodo-α-D-galactopyranoside
• CAS: 548460-30-6
• 化学式: C₂₂H₂₅IO₅
• 分子量: 496.342
• InChiKey: FUYSIGTVHMQPTE-TVONUNMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  acetyl 3,4-di-O-benzyl-2,6-dideoxy-2-iodo-α-D-galactopyranoside 、 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-(3,4-di-O-benzyl-2,6-dideoxy-2-iodo-β-D-galactopyranosyl)-(1->3)-α-D-glucopyranoside 、 methyl 4,6-benzylidene-2-O-benzoyl-3-O-(3,4-di-O-benzyl-2,6-dideoxy-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 、 3,4-di-O-benzyl-6-deoxy-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 3,4-di-O-benzyl-2,6-dideoxy-2-iodo-β-D-galactopyranoside 、 acetyl 3,4-di-O-benzyl-2,6-dideoxy-2-iodo-α-D-galactopyranoside
  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