3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranosyl chloride | 1381871-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranosyl chloride
• CAS: 1381871-17-5
• 化学式: C₄₁H₄₃ClO₈S
• 分子量: 731.307
• InChiKey: DWOMHYXQUCVBIG-WEOXEBIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.81
• 重原子数：
  51.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4,7-tri-O-benzyl-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside 、 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranosyl chloride 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 120.0h， 以890 mg的产率得到methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranosyl-(2->5)-3,4,7-tri-O-benzyl-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside
  参考文献：
  名称：

  Synthesis of sulfonic acid-containing maltose-type keto-oligosaccharides by an iterative approach

  摘要：

  Two different series of (2 -> 5)-alpha-linked homologous keto-oligosaccharides up to tri- and tetrasaccharide were synthesized by an iterative approach, using 3,4,7-tri-O-benzyl-5-O-(2-naphthyl)methyl-1-deoxy-1-ethoxysulfonyl-alpha-D-gluco-hept-2-ulopyranosyl chloride as a key building block. An iterative cycle consisted of a glycosylation step followed by selective cleavage of the (2-naphthyl)methyl group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.067
• 作为产物：
  描述：

  2,3,6-tri-O-benzyl-4-O-((2-naphthyl)methyl)-α,β-D-glucopyranose 在 吡啶 、 正丁基锂 、 氯化亚砜 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranosyl chloride
  参考文献：
  名称：

  Synthesis of sulfonic acid-containing maltose-type keto-oligosaccharides by an iterative approach

  摘要：

  Two different series of (2 -> 5)-alpha-linked homologous keto-oligosaccharides up to tri- and tetrasaccharide were synthesized by an iterative approach, using 3,4,7-tri-O-benzyl-5-O-(2-naphthyl)methyl-1-deoxy-1-ethoxysulfonyl-alpha-D-gluco-hept-2-ulopyranosyl chloride as a key building block. An iterative cycle consisted of a glycosylation step followed by selective cleavage of the (2-naphthyl)methyl group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.067