methyl (2S,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-3,5-diacetyloxy-6-(2,2-dimethylpropanoyloxymethyl)oxan-4-yl]oxy-4-acetyloxy-5-(diacetylamino)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate | 282713-93-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-3,5-diacetyloxy-6-(2,2-dimethylpropanoyloxymethyl)oxan-4-yl]oxy-4-acetyloxy-5-(diacetylamino)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 282713-93-3
• 化学式: C₄₆H₆₈N₂O₂₇
• 分子量: 1081.04
• InChiKey: XULZPHRDBUOLQF-QFJVVKLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  75
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  373
• 氢给体数：
  3
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  methyl (2S,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-3,5-diacetyloxy-6-(2,2-dimethylpropanoyloxymethyl)oxan-4-yl]oxy-4-acetyloxy-5-(diacetylamino)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 、 Phenyl (2,3,4,6-tetra-O-acetyl-β-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-naphthylmethyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 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 2.0h， 以79%的产率得到methyl (2S,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-5-acetamido-2-[[(2R,3R,4R,5S,6R)-3-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(naphthalen-2-ylmethoxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3-hydroxy-6-methoxyoxan-4-yl]oxy-3,5-diacetyloxy-6-(2,2-dimethylpropanoyloxymethyl)oxan-4-yl]oxy-4-acetyloxy-5-(diacetylamino)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  由O型糖蛋白完全合成唾液酸化和硫酸化的寡糖

  摘要：

  已经完成了唾液酸化和硫酸化的寡糖1的全合成，该寡糖1代表了在呼吸粘蛋白中发生的结构。我们的策略取决于使用2-萘甲基（NAP）保护羟基功能。由于其相对于母体化合物14的糖基化反应增强了反应性，因此选择了明确定义的唾液酸供体15。

  DOI：

  10.1016/s0040-4039(00)00261-6
• 作为产物：
  描述：

  methyl 2β-phenylthio-4,7,8,9-tetra-O-acetyl-N,N-diacetylneuraminate 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 methyl (2S,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-3,5-diacetyloxy-6-(2,2-dimethylpropanoyloxymethyl)oxan-4-yl]oxy-4-acetyloxy-5-(diacetylamino)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  由O型糖蛋白完全合成唾液酸化和硫酸化的寡糖

  摘要：

  已经完成了唾液酸化和硫酸化的寡糖1的全合成，该寡糖1代表了在呼吸粘蛋白中发生的结构。我们的策略取决于使用2-萘甲基（NAP）保护羟基功能。由于其相对于母体化合物14的糖基化反应增强了反应性，因此选择了明确定义的唾液酸供体15。

  DOI：

  10.1016/s0040-4039(00)00261-6

文献信息

• The 2-Naphthylmethyl (NAP) Group in Carbohydrate Synthesis: First Total Synthesis of the GlyCAM-1 Oligosaccharide Structures
  作者：Jie Xia、James L. Alderfer、Conrad. F. Piskorz、Khushi L. Matta

  DOI：10.1002/1521-3765(20010119)7:2<356::aid-chem356>3.0.co;2-e

  日期：2001.1.19

  Total syntheses of the GlyCAM-1 (glycosylation-dependent cell adhesion molecule-1) oligosaccharide structures: [alpha-NeuAc-(2 --> 3)-beta-Gal-(1 --> 4)-[alpha-Fuc-(1 --> 3)]-beta-(6-O-SO3Na)-GlcNAc-(1 --> 6)]-[alpha-NeuAc-(2 --> 3)-beta-Gal-(1 --> 3)]-alpha-GalNAc-OMe (1) and [alpha-NeuAc-(2 --> 3)-beta-Gal-(1 --> 4)-[alpha-Fuc-(1 --> 3)]-beta-GlcNAc-(1 --> 6)]-[alpha-NeuAc-(2 3)-beta-Gal-(1 --> 3)]-alpha-GalNAc-OMe (2) through a novel sialyl LewisX tetrasaccharide donor are described. Employing sequential glycosylation strategy, the starting trisaccharide was regio- and stereoselectively constructed through coupling of a disaccharide imidate with the monosaccharide acceptor phenyl-6-O-naphthylmethyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside with TMSOTf as a catalyst without affecting the SPh group. The novel sialyl Lewisx tetrasaccharide donor 3 was then obtained by alpha-L-fucosylation of trisaccharide acceptor with the 2,3,4-tri-O-benzyl-1-thio-beta-L-fucoside donor. The structure of the novel sialyl Lewisx tetrasaccharide was established by a combination of 2D DQF-COSY and 2D ROESY experiments. Target oligosaccharides 1 and 2 were eventually constructed through heptasaccharide which was obtained by regioselective assembly of advanced sialyl Lewisx tetrasaccharide donor 3 and a sialylated trisaccharide acceptor in a predictable and controlled manner. Finally, target heptasaccharides 1 and 2 were fully characterized by 2D DQF-COSY, 2D ROESY, HSQC, HMBC experiments and FAB mass spectroscopy.