N-{[(2R,3S,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl}-4-methyl-N-phenylbenzenesulfonamide | 1421679-05-1

• 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: N-{[(2R,3S,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl}-4-methyl-N-phenylbenzenesulfonamide
• 英文别名: N-[[(2R,3S,4R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl]-4-methyl-N-phenylbenzenesulfonamide
• CAS: 1421679-05-1
• 化学式: C₄₁H₄₁NO₆S
• 分子量: 675.846
• InChiKey: XFAOFXWLXKITIY-MHEUVVKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  对甲苯硫酰苯胺 、 2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hex-1-enitol 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到N-{[(2R,3S,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl}-4-methyl-N-phenylbenzenesulfonamide
  参考文献：
  名称：

  SN2 substitution reaction of 2-C-acetoxymethyl glycals catalyzed by iodine: a novel synthesis of 2-C-N-arylamidomethyl glycals

  摘要：

  The reaction of 2-C-acetoxymethyl glycals with N-aryl amides such as N-aryltosyl amine, p-toluenesulfonamide, and t-butoxycarbonyl amine in the presence of a catalytic amount of iodine affords a novel class of 2-C-N-arylamidomethyl glycals through direct attack at the C-2 position bearing the acetyl group under mild reaction conditions. The use of iodine makes this method simple, convenient, and cost-effective. This is the first report on nucleophilic substitution of 2-C-acetoxymethyl glycals with N-aryl amides using molecular iodine as a catalyst. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.106