2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate | 1357000-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
• CAS: 1357000-46-4
• 化学式: C₄₀H₅₃Cl₃N₂O₂₅
• 分子量: 1068.22
• InChiKey: LSYBYZKYUZPNCG-CMGYGIDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  70.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  345.03
• 氢给体数：
  2.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  8-(p-iodophenyl) octanol 、 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以15%的产率得到2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl orthoester
  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：

  在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 77.5h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
  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