methyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside | 132488-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside
• CAS: 132488-48-3
• 化学式: C₁₇H₂₃NO₇
• 分子量: 353.372
• InChiKey: BQXAGUXLANKRHQ-HDKMNVHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  95.48
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 在 barium dihydroxide 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 4 A molecular sieve 、 氰化汞 、 sodium cyanoborohydride 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 barium(II) oxide 作用下， 以 硝基甲烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 95.0h， 生成 methyl 2-acetamido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-<2,3,6-tri-O-acetyl-4-O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-β-D-glucopyranosyl>-3-O-benzyl-2-deoxy-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-乙酰氨基-2-脱氧-beta-D-吡喃葡萄糖胺 在 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 62.0h， 生成 methyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside
  参考文献：
  名称：

  一种磺达肝葵钠二糖中间体片段BA及其合成方 法

  摘要：

  本发明公开了一种磺达肝葵钠二糖中间体片段BA及其合成方法。本发明合成策略新颖，原料简单易得，反应步数相对较少，反应条件温和，后处理条件简单易操作，生产成本低、收率较高，适合大规模的工业化生产。

  公开号：

  CN102898487B