2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranosyl-(1-4)-2,3-di-O-acetyl-4-tert-butyldimethylsilyl-β-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 293298-83-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranosyl-(1-4)-2,3-di-O-acetyl-4-tert-butyldimethylsilyl-β-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• CAS: 293298-83-6
• 化学式: C₄₆H₇₈O₂₁Si₂
• 分子量: 1023.28
• InChiKey: DXMDUUYQFUWCFB-DNINJBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  69.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  233.03
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranosyl-(1-4)-2,3-di-O-acetyl-4-tert-butyldimethylsilyl-β-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 sodium azide 、 溴 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (2R,3S,4S,5R,6R)-2-Azidomethyl-6-[(2R,3S,4R,5R,6R)-2-azidomethyl-4,5-dihydroxy-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Large Oligosaccharide-Based Glycodendrimers Synthetic Carbohydrate Dendrimers, Part 9: for Part 8, see: W. B. Turnbull, A. R. Pease, J. F. Stoddart, ChemBioChem 2000, 1, 70–74.

  摘要：

  Carbohydrate-based dendritic structures composed of 21 and 27 monosaccharide residues have been synthesized in a convergent manner from trisaccharide building blocks. The oligosaccharide AB, monomers are based on a maltosylbeta(1 --> 6)galactose structure, which has been modified to include two methylamino groups at the primary positions of the glucosyl residues. Reductive alkylation of the secondary amino groups, with the innate formyl function of a second oligosaccharide monomer, allows for the chemoselective construction of dendritic wedges. while employing a minimal number of protecting groups. The first-generation dendron can be coupled either to another AB? monomer, to give a second-generation dendron, or to a tris[2-(methylamino)ethyl] a mine-based core moiety, to provide a carbohydrate-based dendrimer. Alternating alpha- and beta-glucosyl residues in the monomers and dendrons, simplifies H-1 NMR spectra as a consequence of spreading out the anomeric proton signals. Monomers and dendrons were characterized by extensive one- and two-dimensional NMR spectroscopy in addition to FAB, electrospray, and MALDI-TOF mass spectrometry. Molecular dynamics simulations revealed similar conformations in the dendrons as in the isolated trisaccharide repeating units.

  DOI：

  10.1002/1521-3765(20020703)8:13<2988::aid-chem2988>3.0.co;2-2
• 作为产物：
  描述：

  乙酸酐 、 在 吡啶 作用下， 以10.4 g的产率得到2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranosyl-(1-4)-2,3-di-O-acetyl-4-tert-butyldimethylsilyl-β-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Large Oligosaccharide-Based Glycodendrimers Synthetic Carbohydrate Dendrimers, Part 9: for Part 8, see: W. B. Turnbull, A. R. Pease, J. F. Stoddart, ChemBioChem 2000, 1, 70–74.

  摘要：

  Carbohydrate-based dendritic structures composed of 21 and 27 monosaccharide residues have been synthesized in a convergent manner from trisaccharide building blocks. The oligosaccharide AB, monomers are based on a maltosylbeta(1 --> 6)galactose structure, which has been modified to include two methylamino groups at the primary positions of the glucosyl residues. Reductive alkylation of the secondary amino groups, with the innate formyl function of a second oligosaccharide monomer, allows for the chemoselective construction of dendritic wedges. while employing a minimal number of protecting groups. The first-generation dendron can be coupled either to another AB? monomer, to give a second-generation dendron, or to a tris[2-(methylamino)ethyl] a mine-based core moiety, to provide a carbohydrate-based dendrimer. Alternating alpha- and beta-glucosyl residues in the monomers and dendrons, simplifies H-1 NMR spectra as a consequence of spreading out the anomeric proton signals. Monomers and dendrons were characterized by extensive one- and two-dimensional NMR spectroscopy in addition to FAB, electrospray, and MALDI-TOF mass spectrometry. Molecular dynamics simulations revealed similar conformations in the dendrons as in the isolated trisaccharide repeating units.

  DOI：

  10.1002/1521-3765(20020703)8:13<2988::aid-chem2988>3.0.co;2-2

文献信息

• Synthesis of lactoside glycodendrons using photoaddition and reductive amination methodologies
  作者：Alshakim Nelson、J Fraser Stoddart

  DOI：10.1016/j.carres.2004.06.011

  日期：2004.8

  Carbohydrate-based divalent and tetravalent lactoside glycodendrons were constructed in a convergent manner. The dendrons were synthesized beginning with the photoaddition of hepta-O-acetyl-1-thio-beta-lactose, in an anti-Markovnikov manner, to a bis-allyl AB(2) trisaccharide to form a divalent dendron. Following two nearly quantitative deprotection steps, the divalent lactoside was coupled to another AB(2) trisaccharide by reductive amination to afford a tetravalent dendron. These paucivalent compounds were characterized by NMR spectroscopy and mass spectrometry. (C) 2004 Elsevier Ltd. All rights reserved.