2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 293298-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-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]-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 293298-82-5
• 化学式: C₃₈H₅₄O₂₃
• 分子量: 878.833
• InChiKey: SVQBNLMCXHFSPC-JPFUOEBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  61
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  267
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成
  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：

  ethyl 2,3,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-D-maltoside 、 双丙酮半乳糖 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 高氯酸 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Glycosylation and Pyranose-Furanose Isomerization of Carbohydrates Using HClO₄-SiO₂: Synthesis of Oligosaccharides Containing Galactofuranose

  摘要：

  一系列含有6-O-连接的呋喃半乳糖的二糖和三糖被合成，它们是以甲基糖苷的异头混合物形式，通过硅胶负载的高氯酸作为催化剂。

  DOI：

  10.1055/s-2007-965913