2-(trimethylsilyl) ethyl β-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1 -> 3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 270248-06-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl) ethyl β-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1 -> 3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: 2-(trimethylsilyl) ethyl β-D-galactopyranosyl-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1-> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 270248-06-1
• 化学式: C₇₉H₉₃NO₂₂Si
• 分子量: 1436.69
• InChiKey: FTDNUPFLQKMEGA-ZLHBZDNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  103.0
• 可旋转键数：
  33.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  287.98
• 氢给体数：
  6.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  苯甲醛二甲缩醛 、 2-(trimethylsilyl) ethyl β-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1 -> 3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以91%的产率得到2-(trimethylsilyl) ethyl 4,6-O-benzylidene-β-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1 -> 3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzyl-β-d-glucopyranoside
  参考文献：
  名称：

  Synthetic sulfated glucuronosyl paragloboside (SGPG) and its use for the detection of autoimmune peripheral neuropathies

  摘要：

  The sulfated glucuronosyl paragloboside SO4-3-GlcA(beta 1-3)Gal-(beta 1-4)GlcNAc(beta 1-3)Gal-(beta 1-4)Glc beta(1-1')Cer (SGPG) is a specific constituent of the peripheral nervous system involved in human dysimmune neuropathies. Although it is highly immunogenic in human pathology, it is not a major constituent of peripheral nerve in humans. Pure SGPG is very difficult to obtain from natural sources, but is needed for the design of efficient and reproducible immunoassays. We describe a new chemical synthesis of this important glycolipid with a stearic tail, including its complete characterization by mass spectrometry and its use in the detection of autoimmune neuropathies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.021
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-(6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到2-(trimethylsilyl) ethyl β-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1 -> 3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic sulfated glucuronosyl paragloboside (SGPG) and its use for the detection of autoimmune peripheral neuropathies

  摘要：

  The sulfated glucuronosyl paragloboside SO4-3-GlcA(beta 1-3)Gal-(beta 1-4)GlcNAc(beta 1-3)Gal-(beta 1-4)Glc beta(1-1')Cer (SGPG) is a specific constituent of the peripheral nervous system involved in human dysimmune neuropathies. Although it is highly immunogenic in human pathology, it is not a major constituent of peripheral nerve in humans. Pure SGPG is very difficult to obtain from natural sources, but is needed for the design of efficient and reproducible immunoassays. We describe a new chemical synthesis of this important glycolipid with a stearic tail, including its complete characterization by mass spectrometry and its use in the detection of autoimmune neuropathies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.021

文献信息

• Synthesis and NMR study of a heptasaccharide, epitope of the stage-specific embryonic antigen-1 (SSEA-1)
  作者：Yongmin Zhang、Bruno Dausse、Pierre Sinaÿ、Mohamed Afsahi、Patrick Berthault、Hervé Desvaux

  DOI：10.1016/s0008-6215(99)00299-2

  日期：2000.3

  This paper describes an efficient synthesis of the beta-2-trimethylsilylethyl glycoside of lacto-N-fucoheptaose based on a highly stereo- and regioselective glycosylation between a Lewis(x) trisaccharidic donor and a tetraol tetrasaccharidic acceptor. The title compound was characterized by high-resolution NMR spectroscopy. (C) 2000 Elsevier Science Ltd. All rights reserved.