6-O-benzyl-3,4-di-O-(carbonyl)-2-deoxy-2-bromo-α-D-galactopyranosyl trichloroacetimidate | 548460-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-O-benzyl-3,4-di-O-(carbonyl)-2-deoxy-2-bromo-α-D-galactopyranosyl trichloroacetimidate
• CAS: 548460-04-4
• 化学式: C₁₆H₁₅BrCl₃NO₆
• 分子量: 503.561
• InChiKey: HDZMGYUAIIPZCH-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.07
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-O-benzyl-3,4-di-O-(carbonyl)-2-deoxy-2-bromo-α-D-galactopyranosyl trichloroacetimidate 、 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-benzyl-3,4-di-O-(carbonyl)-2-deoxy-2-bromo-β-D-galactopyranosyl)-(1->3)-α-D-glucopyranoside 、 methyl 4,6-benzylidene-2-O-benzoyl-3-O-(6-O-benzyl-3,4-di-O-(carbonyl)-2-deoxy-2-bromo-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：

  1,5-anhydro-6-O-benzyl-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose 在 N-溴代丁二酰亚胺(NBS) 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 6-O-benzyl-3,4-di-O-(carbonyl)-2-deoxy-2-bromo-α-D-galactopyranosyl trichloroacetimidate
  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