3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl N-methyl-p-toluenesulfonamide

• 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: 3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl N-methyl-p-toluenesulfonamide
• 英文别名: N-[(2R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]-N,4-dimethylbenzenesulfonamide
• 化学式: C₃₅H₃₉NO₆S
• 分子量: 601.764
• InChiKey: GKFRTHNARRWUKA-BAQBVXSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,6-三邻苄基半乳醛 、 N-甲基对甲苯磺酰胺 在 三苯基膦氢溴酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以70%的产率得到3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl N-methyl-p-toluenesulfonamide
  参考文献：
  名称：

  A Novel Sulfonamidoglycosylation of Glycals

  摘要：

  The sulfonamidoglycosylation of benzylated glycals using a catalytic amount of triphenylphosphine hydrobromide proceeded in a highly stereoselective fashion to give the beta anomers with good to high yields, This process was demonstrated with D-galactal and D-glucal. Two of the new N-2-(deoxyglycosyl)sulfonamides were tested as inhibitors of tumor cell growth in vitro and showed anti proliferative properties in the micromolar range.

  DOI：

  10.1021/ol035838g

文献信息

• A Novel Sulfonamidoglycosylation of Glycals
  作者：Pedro A. Colinas、Rodolfo D. Bravo

  DOI：10.1021/ol035838g

  日期：2003.11.1

  The sulfonamidoglycosylation of benzylated glycals using a catalytic amount of triphenylphosphine hydrobromide proceeded in a highly stereoselective fashion to give the beta anomers with good to high yields, This process was demonstrated with D-galactal and D-glucal. Two of the new N-2-(deoxyglycosyl)sulfonamides were tested as inhibitors of tumor cell growth in vitro and showed anti proliferative properties in the micromolar range.