p-octyloxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-1-thio-α-D-mannopyranoside | 1357000-53-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: p-octyloxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-(4-octoxyphenyl)sulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1357000-53-3
• 化学式: C₄₀H₅₇NO₁₇S
• 分子量: 855.955
• InChiKey: OGRWQNWEJVSTTA-YPAKVSGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  59
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  249
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside 、 p-octyloxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-1-thio-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以86%的产率得到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 吡啶 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 一水合肼 、 溶剂黄146 、 三苯基膦 、 lithium iodide 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 氯仿 、 水 、 甲苯 、 乙腈 为溶剂， 反应 25.0h， 生成 p-octyloxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-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