4-methoxyphenyl (2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside | 1221254-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
• CAS: 1221254-76-7
• 化学式: C₆₁H₇₃NO₂₉
• 分子量: 1284.24
• InChiKey: WXPYJSNAQMKTTB-FPRKTIOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  91.0
• 可旋转键数：
  21.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  353.42
• 氢给体数：
  2.0
• 氢受体数：
  29.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl (2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 、 5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-双脱氧-2-S-苯基-2-硫基-D- 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.5h， 以53%的产率得到4-methoxyphenyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->6)-(2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Concise synthesis of the pentasaccharide O-antigen corresponding to the Shiga toxin producing Escherichia coli O171

  摘要：

  An expedient total synthesis of a pentasaccharide as its 4-methoxyphenyl glycoside corresponding to the Shiga toxin producing Escherichia coli O171 has been achieved for the first time in excellent yield. Most of the glycosylation steps are highly stereoselective. Stereoselective glycosylation of sialic acid derivative was obtained exploiting the nitrile effect of the solvent used. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2010.01.001
• 作为产物：
  描述：

  在 Pearlman's catalist 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以1.4 g的产率得到4-methoxyphenyl (2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Concise synthesis of the pentasaccharide O-antigen corresponding to the Shiga toxin producing Escherichia coli O171

  摘要：

  An expedient total synthesis of a pentasaccharide as its 4-methoxyphenyl glycoside corresponding to the Shiga toxin producing Escherichia coli O171 has been achieved for the first time in excellent yield. Most of the glycosylation steps are highly stereoselective. Stereoselective glycosylation of sialic acid derivative was obtained exploiting the nitrile effect of the solvent used. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2010.01.001