p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside | 873298-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside
• 英文别名: [(4aR,6S,7R,8S,8aS)-6-(4-methylphenyl)sulfanyl-2-phenyl-8-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• CAS: 873298-76-1
• 化学式: C₆₁H₆₀O₁₁S
• 分子量: 1001.21
• InChiKey: JEJYPXDZNPLMMN-XXFDCHMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  73
• 可旋转键数：
  21
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 、 methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 六氢-1-(苯基硫代)-2H-氮杂卓-2-酮 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以103.9 mg的产率得到methyl 2,3,6-tri-O-benzyl-4-O-[2'-O-benzoyl-4',6'-O-benzylidene-3'-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside
  参考文献：
  名称：

  A new one-pot synthesis of Gb3 and isoGb3 trisaccharide analogues

  摘要：

  Gb(3) and isoGb(3) are both biologically important oligosaccharides. A new efficient synthesis of Gb(3) and isoGb(3) trisaccharide analogues has been achieved by one-pot sequential glycosylation strategy starting from simple monosaccharide building blocks promoted by N-(phenylthio)-epsilon-caprolactam at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.058
• 作为产物：
  描述：

  (p-methylphenyl) 4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 六氢-1-(苯基硫代)-2H-氮杂卓-2-酮 、 三氟甲磺酸酐 、 potassium iodide 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  A new one-pot synthesis of Gb3 and isoGb3 trisaccharide analogues

  摘要：

  Gb(3) and isoGb(3) are both biologically important oligosaccharides. A new efficient synthesis of Gb(3) and isoGb(3) trisaccharide analogues has been achieved by one-pot sequential glycosylation strategy starting from simple monosaccharide building blocks promoted by N-(phenylthio)-epsilon-caprolactam at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.058

文献信息

• A new one-pot synthesis of Gb3 and isoGb3 trisaccharide analogues
  作者：Changning Wang、Qin Li、Haisheng Wang、Li-He Zhang、Xin-Shan Ye

  DOI：10.1016/j.tet.2006.09.058

  日期：2006.12

  Gb(3) and isoGb(3) are both biologically important oligosaccharides. A new efficient synthesis of Gb(3) and isoGb(3) trisaccharide analogues has been achieved by one-pot sequential glycosylation strategy starting from simple monosaccharide building blocks promoted by N-(phenylthio)-epsilon-caprolactam at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.