2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside | 1357000-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside
• CAS: 1357000-54-4
• 化学式: C₂₄H₂₉IO₁₁
• 分子量: 620.392
• InChiKey: MWEFRBHXVYJCGT-XNBWIAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  132.89
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 甲酸 、 三氟甲磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-(4-iodophenyl)ethyl 6-O-[2-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-2,3,4-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  放射性碘化三糖衍生物的替代合成，2-(4-125碘苯基)乙基 2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基-(1→2)-α-D-吡喃甘露糖基-(1→6)-β-D -吡喃葡萄糖苷及其具有不同长度烷基链而不是乙基的类似物的制备：用于体内成像的N-乙酰氨基葡糖转移酶V的受体底物

  摘要：

  A radioiodinated artificial substrate of N-acetylglucosaminyltransferase V (GnT-V), 2-(4-iodophenyl)ethyl 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 -> 2)-alpha-D-mannopyranosyl-(1 -> 6)-beta-D-glucopyranoside (([I-125]1a), was alternatively synthesized by using the glycosylation reaction from the non-reducing end, in which a glycosyl sulfoxide and a thioglycoside were employed as the glycosyl acceptor and donor, respectively. In addition, two derivatives of [I-125]1a having different lengths of alkyl chain ([I-125]1b, [I-125]1c) were prepared in the same way to increase the permeability of the substrates through the cell membrane and into the Golgi apparatus, where GnT-V acts to modify glycoconjugates by transferring N-acetylglucosamine units from UDP-GIcNAc.

  DOI：

  10.3987/com-11-12332
• 作为产物：
  描述：

  4-碘苯乙醇 、 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以62%的产率得到2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside
  参考文献：
  名称：

  放射性碘化三糖衍生物的替代合成，2-(4-125碘苯基)乙基 2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基-(1→2)-α-D-吡喃甘露糖基-(1→6)-β-D -吡喃葡萄糖苷及其具有不同长度烷基链而不是乙基的类似物的制备：用于体内成像的N-乙酰氨基葡糖转移酶V的受体底物

  摘要：

  A radioiodinated artificial substrate of N-acetylglucosaminyltransferase V (GnT-V), 2-(4-iodophenyl)ethyl 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 -> 2)-alpha-D-mannopyranosyl-(1 -> 6)-beta-D-glucopyranoside (([I-125]1a), was alternatively synthesized by using the glycosylation reaction from the non-reducing end, in which a glycosyl sulfoxide and a thioglycoside were employed as the glycosyl acceptor and donor, respectively. In addition, two derivatives of [I-125]1a having different lengths of alkyl chain ([I-125]1b, [I-125]1c) were prepared in the same way to increase the permeability of the substrates through the cell membrane and into the Golgi apparatus, where GnT-V acts to modify glycoconjugates by transferring N-acetylglucosamine units from UDP-GIcNAc.

  DOI：

  10.3987/com-11-12332