β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 629624-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: O¹,O²;O³,O⁴-diisopropylidene-O⁶-β-lactosyl-α-D-galactopyranose；O¹,O²;O³,O⁴-Diisopropyliden-O⁶-β-lactosyl-α-D-galactopyranose；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 629624-92-6
• 化学式: C₂₄H₄₀O₁₆
• 分子量: 584.572
• InChiKey: CQMVOVZQQDYCMN-GLEXPJKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  225
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 St₃-Fusion 、 三氟乙酸 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 反应 15.0h， 生成 (5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->3)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-D-galactopyranose
  参考文献：
  名称：

  Chemically Defined Sialoside Scaffolds for Investigation of Multivalent Interactions with Sialic Acid Binding Proteins^†

  摘要：

  Four glycodendrons and a glycocluster were synthesized fromcarbohydrate building blocks to form paucivalent (di- to tetravalent) structures of controlled scaffold architectures. Enzymatic sialylation of the functionalized cluster and dendrons, terminated in lactose residues, generated a library of paucivalent synthetic sialosides displaying sialic acids with different dispositions. These newly constructed bioactive sialic acid-based structures were differentially recognized by sialoadhesin, a mammalian macrophage sialic acid binding protein. The binding of the sialosides to sialoadhesin was evaluated by an enzyme-linked immunosorbant assay to investigate the complementarity of scaffold structure and binding to sialoadhesin. Modulating the interaction between sialoadhesin and its sialic acid ligands has important implications in immunobiology.

  DOI：

  10.1021/jo030203g
• 作为产物：
  描述：

  2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1,6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以83%的产率得到β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Chemically Defined Sialoside Scaffolds for Investigation of Multivalent Interactions with Sialic Acid Binding Proteins^†

  摘要：

  Four glycodendrons and a glycocluster were synthesized fromcarbohydrate building blocks to form paucivalent (di- to tetravalent) structures of controlled scaffold architectures. Enzymatic sialylation of the functionalized cluster and dendrons, terminated in lactose residues, generated a library of paucivalent synthetic sialosides displaying sialic acids with different dispositions. These newly constructed bioactive sialic acid-based structures were differentially recognized by sialoadhesin, a mammalian macrophage sialic acid binding protein. The binding of the sialosides to sialoadhesin was evaluated by an enzyme-linked immunosorbant assay to investigate the complementarity of scaffold structure and binding to sialoadhesin. Modulating the interaction between sialoadhesin and its sialic acid ligands has important implications in immunobiology.

  DOI：

  10.1021/jo030203g

文献信息

• Freudenberg et al., Chemische Berichte, 1928, vol. 61, p. 1735,1738
  作者：Freudenberg et al.

  DOI：——

  日期：——
• Glycosylation Using Unprotected Alkynyl Donors
  作者：Sreeman K. Mamidyala、M.G. Finn

  DOI：10.1021/jo901857x

  日期：2009.11.6

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.
• Chemically Defined Sialoside Scaffolds for Investigation of Multivalent Interactions with Sialic Acid Binding Proteins^†
  作者：Stacey A. Kalovidouris、Ola Blixt、Alshakim Nelson、Sébastien Vidal、W. Bruce Turnbull、James C. Paulson、J. Fraser Stoddart

  DOI：10.1021/jo030203g

  日期：2003.10.1

  Four glycodendrons and a glycocluster were synthesized fromcarbohydrate building blocks to form paucivalent (di- to tetravalent) structures of controlled scaffold architectures. Enzymatic sialylation of the functionalized cluster and dendrons, terminated in lactose residues, generated a library of paucivalent synthetic sialosides displaying sialic acids with different dispositions. These newly constructed bioactive sialic acid-based structures were differentially recognized by sialoadhesin, a mammalian macrophage sialic acid binding protein. The binding of the sialosides to sialoadhesin was evaluated by an enzyme-linked immunosorbant assay to investigate the complementarity of scaffold structure and binding to sialoadhesin. Modulating the interaction between sialoadhesin and its sialic acid ligands has important implications in immunobiology.