Phenyl (6-O-pivaloyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside | 329783-71-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl (6-O-pivaloyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS: 329783-71-3
• 化学式: C₇₂H₇₇NO₁₆S
• 分子量: 1244.47
• InChiKey: DVDKZMUZEJODNU-BNCLKZELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.0
• 重原子数：
  90.0
• 可旋转键数：
  22.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  185.44
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  Methyl (2,3,4-tri-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside 、 Phenyl (6-O-pivaloyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以32%的产率得到Phenyl (6-O-pivaloyl-2,3,4-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-[(6-O-pivaloyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)]-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-2-deoxy-6-O-naphthylmethyl-2-phthalimido-β-D-gluco...
  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：

  phenyl (2,3,4-tri-O-acetyl-6-O-trimethylacetyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 Phenyl (6-O-pivaloyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-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