Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside | 329783-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: methyl (2S,4S,5R,6R)-4-acetyloxy-5-(diacetylamino)-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(2,2-dimethylpropanoyloxymethyl)-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-hydroxy-2-(naphthalen-2-ylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 329783-76-8
• 化学式: C₆₈H₇₈N₂O₂₇S
• 分子量: 1387.43
• InChiKey: DEAFQGYHAYUSDU-RQNQNMCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  98
• 可旋转键数：
  33
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  386
• 氢给体数：
  1
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以100%的产率得到C₇₀H₈₀N₂O₂₈S
  参考文献：
  名称：

  The 2-Naphthylmethyl (NAP) Group in Carbohydrate Synthesis: First Total Synthesis of the GlyCAM-1 Oligosaccharide Structures

  摘要：

  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.

  DOI：

  10.1002/1521-3765(20010119)7:2<356::aid-chem356>3.0.co;2-e
• 作为产物：
  描述：

  Benzyl 6-O-pivaloyl-β-D-galactopyranoside 在 10percent Pd/C 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 4 A molecular sieve 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 47.5h， 生成 Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  The 2-Naphthylmethyl (NAP) Group in Carbohydrate Synthesis: First Total Synthesis of the GlyCAM-1 Oligosaccharide Structures

  摘要：

  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.

  DOI：

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