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 | 153658-94-7

• 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-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
• 英文别名: 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；[(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-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 153658-94-7
• 化学式: C₃₈H₅₄O₂₃
• 分子量: 878.833
• InChiKey: SVQBNLMCXHFSPC-GGYTVOHOSA-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-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 St₃-Fusion 、 sodium methylate 、 三氟乙酸 、 manganese(ll) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 21.0h， 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：

  [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-[3-(2-oxochromen-7-yl)oxypropylsulfanyl]oxan-3-yl]oxyoxan-2-yl]methyl acetate 、 双丙酮半乳糖 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到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
  参考文献：
  名称：

  3-Mercaptopropanol as a Traceless Linker for Chemical and Enzymatic Synthesis of Oligosaccharides

  摘要：

  The reducing end of protected carbohydrates can be equipped with a series of aglycones via the photochemical installation of a 3-mercaptoethanol linker. This linker is stable during chemical and enzymatic glycosylation reactions but can be activated readily and efficiently to couple oligosaccharides with different nucleophiles. This approach provides straightforward access to a range of molecules that serve as probes for carbohydrate modifying enzymes.

  DOI：

  10.1021/ol062922y

文献信息

• Amberlyst 15 as a mild and effective activator for the glycosylation with disarmed glycosyl trichloroacetimidate donors
  作者：Qiang Tian、Shuo Zhang、Qian Yu、Mei-Bo He、Jin-Song Yang

  DOI：10.1016/j.tet.2006.12.091

  日期：2007.3

  Amberlyst 15 acidic resin has been shown to be a mild and effective activator for the glycosylation with commonly used disarmed glycosyl trichloroacetimidate donors. Glucosylation, galactosylation, rhamnosylation, and lactosylation of a panel of representative alcohol and thiol acceptors promoted by Amberlyst 15 allowed for the formation of structurally diverse O- or S-linked oligosaccharides and glycosylated

  Amberlyst 15酸性树脂已被证明是一种温和有效的活化剂，可用于与常用的脱甲糖基三氯乙酰亚氨酸酯供体进行糖基化反应。由Amberlyst 15促进的一组代表性醇和硫醇受体的糖基化，半乳糖基化，鼠李糖基化和乳糖基化可以中等至极好的产率形成结构多样的O或S联寡糖和糖基化氨基酸。
• Glycosylation and Pyranose-Furanose Isomerization of Carbohydrates Using HClO₄-SiO₂: Synthesis of Oligosaccharides Containing Galactofuranose
  作者：Anup Misra、Chinmoy Mukherjee

  DOI：10.1055/s-2007-965913

  日期：2007.3

  A series of di- and trisaccharides containing 6-O-linked galactofuranose were synthesized as an anomeric mixture of methyl glycosides using silica-supported perchloric acid.

  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。
• Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism
  作者：Hirosato Kondo、Shin Aoki、Yoshitaka Ichikawa、Randall L. Halcomb、Helena Ritzen、Chi-Huey Wong

  DOI：10.1021/jo00083a032

  日期：1994.2

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.