Benzyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-α-ulopyranosyl)onate]-(2->3)-6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranoside | 329783-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-α-ulopyranosyl)onate]-(2->3)-6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranoside
• CAS: 329783-79-1
• 化学式: C₄₄H₅₉NO₂₂
• 分子量: 953.946
• InChiKey: KVCSUNHIVYPJKU-RKMUWRJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  67.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  284.7
• 氢给体数：
  0.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  Benzyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-α-ulopyranosyl)onate]-(2->3)-6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranoside 在 10percent Pd/C 三氟甲磺酸三甲基硅酯 、 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 为溶剂， 反应 27.5h， 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
• 作为产物：
  描述：

  Benzyl 6-O-pivaloyl-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 3 A molecular sieve 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 Benzyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-α-ulopyranosyl)onate]-(2->3)-6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranoside
  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