p-octyloxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthaloylamino-β-D-glucopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside | 1357000-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-octyloxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthaloylamino-β-D-glucopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS: 1357000-49-7
• 化学式: C₅₄H₆₁NO₁₅S
• 分子量: 996.142
• InChiKey: JXIWDMJOBSVNPQ-ADWLJYPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.14
• 重原子数：
  71.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  180.89
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  p-octyloxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthaloylamino-β-D-glucopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三甲基氯硅烷 、 三氟甲磺酸 、 一水合肼 、 溶剂黄146 、 lithium iodide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 甲苯 为溶剂， 反应 25.5h， 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：

  3,4,6-tri-O-acetyl-2-N-phthaloyl-β(1-2)-D-glucosaminyl-3-O-benzyl-(4,6)-benzylidene-β-D-mannopyranosyl p-octyloxyphenyl sulfoxide 在 三苯基膦 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 2.0h， 以92%的产率得到p-octyloxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthaloylamino-β-D-glucopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
  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