methyl 2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-6-O-<4-O-(3-O-methyl-β-D-galactopyranosyl)-β-D-glucopyranosyl>-β-D-glucopyranoside | 132410-58-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-6-O-<4-O-(3-O-methyl-β-D-galactopyranosyl)-β-D-glucopyranosyl>-β-D-glucopyranoside
• CAS: 132410-58-3
• 化学式: C₂₈H₄₉NO₂₁
• 分子量: 735.691
• InChiKey: PBLBRQLAVBNNPJ-MVBPJKBBSA-N

物化性质

• 沸点：
  1083.3±65.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -8.3
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  334.7
• 氢给体数：
  12.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-6-O-<4-O-(3-O-methyl-β-D-galactopyranosyl)-β-D-glucopyranosyl>-β-D-glucopyranoside 、 alkaline earth salt of/the/ methylsulfuric acid 以33.8%的产率得到methyl 2-acetamido-2-deoxy-4-O-(3-O-(α-D-N-acetylneuraminyl)-β-D-galactopyranosyl)-6-O-<4-O-(3-O-methyl-β-D-galactopyranosyl)-β-D-glucopyranosyl>-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic oligosaccharides related to group B streptococcal polysaccharides. 5. Combined chemical and enzymic synthesis of a pentasaccharide repeating unit of the capsular polysaccharide of type III group B Streptococcus and one- and two-dimensional NMR spectroscopic studies

  摘要：

  A combination of chemical and enzymatic methods is described for the synthesis of the branching pentasaccharide 3-OMe-beta-D-Galp-(1 --> 4)-beta-D-Glcp-(1 --> 6)-[alpha-D-Neup5Ac-(2 --> 3)-beta-D-Galp-(1 --> 4)]-beta-D-GlcpNAc-OMe (4). Pentasaccharide 4, represents a complete repeating unit of the capsular polysaccharide of type III group B Streptococci, which will be used as a molecular probe in the study of the fine specificities of carbohydrate-protein interactions. Key intermediate was the alcohol methyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxy-benzyl)-beta-D-glucopyranoside (9), which was beta-D-galactosylated and chemoselectively deprotected to provide the beta-D-Galp-beta-D-GlcpNAc acceptor block 13. Two approaches are described for the synthesis of the beta-D-Galp-(1 --> 4)-beta-D-Glcp donor block 17, which was coupled to acceptor 13 under the agency of trimethylsilyl trifluoromethanesulfonate. Removal of the blocking groups from the fully protected tetrasaccharide 24 by transesterification and hydrogenolysis provided tetrasaccharide 5, which was sialylated enzymatically using a specific rat liver sialyltransferase to provide pentasaccharide 4. Complete assignment of the H-1 and C-13 NMR spectra of the tetra-5 and pentasaccharide 4 is presented, and their carbon spin-lattice relaxation times (T1) are also reported.

  DOI：

  10.1021/jo00010a037
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氢气 、 sodium methylate 、 氰化汞 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 硝基甲烷 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 87.0h， 生成 methyl 2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-6-O-<4-O-(3-O-methyl-β-D-galactopyranosyl)-β-D-glucopyranosyl>-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic oligosaccharides related to group B streptococcal polysaccharides. 5. Combined chemical and enzymic synthesis of a pentasaccharide repeating unit of the capsular polysaccharide of type III group B Streptococcus and one- and two-dimensional NMR spectroscopic studies

  摘要：

  A combination of chemical and enzymatic methods is described for the synthesis of the branching pentasaccharide 3-OMe-beta-D-Galp-(1 --> 4)-beta-D-Glcp-(1 --> 6)-[alpha-D-Neup5Ac-(2 --> 3)-beta-D-Galp-(1 --> 4)]-beta-D-GlcpNAc-OMe (4). Pentasaccharide 4, represents a complete repeating unit of the capsular polysaccharide of type III group B Streptococci, which will be used as a molecular probe in the study of the fine specificities of carbohydrate-protein interactions. Key intermediate was the alcohol methyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxy-benzyl)-beta-D-glucopyranoside (9), which was beta-D-galactosylated and chemoselectively deprotected to provide the beta-D-Galp-beta-D-GlcpNAc acceptor block 13. Two approaches are described for the synthesis of the beta-D-Galp-(1 --> 4)-beta-D-Glcp donor block 17, which was coupled to acceptor 13 under the agency of trimethylsilyl trifluoromethanesulfonate. Removal of the blocking groups from the fully protected tetrasaccharide 24 by transesterification and hydrogenolysis provided tetrasaccharide 5, which was sialylated enzymatically using a specific rat liver sialyltransferase to provide pentasaccharide 4. Complete assignment of the H-1 and C-13 NMR spectra of the tetra-5 and pentasaccharide 4 is presented, and their carbon spin-lattice relaxation times (T1) are also reported.

  DOI：

  10.1021/jo00010a037