p-methoxyphenyl 3,4,7-tri-O-benzyl-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-ulopyranosyl-(2->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 1381871-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,4,7-tri-O-benzyl-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-ulopyranosyl-(2->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: ethyl [(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6S)-6-(ethoxysulfonylmethyl)-6-[(2R,3R,4S,5R,6S)-6-(4-methoxyphenoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-hydroxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methanesulfonate
• CAS: 1381871-23-3
• 化学式: C₉₄H₁₀₄O₂₃S₂
• 分子量: 1665.98
• InChiKey: NFBUGNVBPRXSQA-ATBSRHRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  119
• 可旋转键数：
  45
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  271
• 氢给体数：
  1
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3,4,7-tri-O-benzyl-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-ulopyranosyl-(2->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium iodide 、 palladium 10% on activated carbon 、 氢气 作用下， 以 丙酮 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 48.0h， 以70%的产率得到p-methoxyphenyl 1-deoxy-1-(sodium sulfonato)-α-D-gluco-hept-2-ulopyranosyl-(2>5)-1-deoxy-1-(sodium sulfonato)-α-D-gluco-hept-2-ulopyranosyl-(2->4)-β-D-glucopyranoside
  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：

  p-methoxyphenyl 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-ulopyranosyl-(2->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以79%的产率得到p-methoxyphenyl 3,4,7-tri-O-benzyl-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-ulopyranosyl-(2->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  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