8-methoxycarbonyloct-1-yl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 56343-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 8-methoxycarbonyloct-1-yl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside；8-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
• CAS: 56343-03-4；71048-95-8；79083-28-6；82863-54-5
• 化学式: C₂₅H₃₇NO₈
• 分子量: 479.571
• InChiKey: MLVKBOGVBGQTML-GHHTZWMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  112.55
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloct-1-yl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 四氢呋喃 、 calcium sulfate 、 sodium methylate 、 氰化汞 作用下， 以 硝基甲烷 、 苯 为溶剂， 反应 4.03h， 生成 (8-Methoxycarbonyloctyl)-<2-acetamido-2-desoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosid>
  参考文献：
  名称：

  Synthesis of the T [β-d-Gal-(1→3)-α-d-GalNAc]-antigenic determinant in a form useful for the preparation of an effective artificial antigen and the corresponding immunoadsorbent

  摘要：

  The T antigenic determinant was synthesized in the form 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl)-alpha-D-galactopyranoside (6) (beta-D-Gal-(1 goes to 3)-alpha-D-GalNAcO(CH2)8CO2Me). This T-hapten was used to prepare a T-BSA artificial antigen (7) and an immunoadsorbent (8), which were shown to possess the expected immunological properties. Nuclear Overhauser enhancements of the signals for anti-periplanar H-2' and the syn-axial H-3' of the beta-D-galactopyranosyl group were observed on saturation of H-1'. The signal for H-3 of the 2-acetamido-2-deoxy-alpha-D-galactopyranoside residue was also enhanced.

  DOI：

  10.1016/s0008-6215(00)80750-8
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 在 palladium on activated charcoal 氢气 、 sodium methylate 、 氰化汞 、 对甲苯磺酸 作用下， 以 硝基甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 81.0h， 生成 8-methoxycarbonyloct-1-yl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the T [β-d-Gal-(1→3)-α-d-GalNAc]-antigenic determinant in a form useful for the preparation of an effective artificial antigen and the corresponding immunoadsorbent

  摘要：

  The T antigenic determinant was synthesized in the form 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl)-alpha-D-galactopyranoside (6) (beta-D-Gal-(1 goes to 3)-alpha-D-GalNAcO(CH2)8CO2Me). This T-hapten was used to prepare a T-BSA artificial antigen (7) and an immunoadsorbent (8), which were shown to possess the expected immunological properties. Nuclear Overhauser enhancements of the signals for anti-periplanar H-2' and the syn-axial H-3' of the beta-D-galactopyranosyl group were observed on saturation of H-1'. The signal for H-3 of the 2-acetamido-2-deoxy-alpha-D-galactopyranoside residue was also enhanced.

  DOI：

  10.1016/s0008-6215(00)80750-8