1,2,3,6-tetra-O-acetyl-4-O-[2,3,4-tri-O-acetyl-6-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose | 391595-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,6-tetra-O-acetyl-4-O-[2,3,4-tri-O-acetyl-6-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose
• 英文别名: TBDMS(-6)Gal2Ac3Ac4Ac(b1-4)a-Man1Ac2Ac3Ac6Ac；[(2R,3R,4S,5S,6R)-4,5,6-triacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 391595-11-2
• 化学式: C₃₂H₅₀O₁₈Si
• 分子量: 750.824
• InChiKey: OYGBXVKICOCRSB-HXFZIAGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  51
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-O-[2,3,4-tri-O-acetyl-6-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose 在 二甲胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以100%的产率得到2,3,6-tri-O-acetyl-4-O-[2,3,4-tri-O-acetyl-6-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose
  参考文献：
  名称：

  Efficient synthesis of the antigenic phosphoglycans of the Leishmania parasite

  摘要：

  利什曼原虫的抗原性磷酸甘露聚糖重复单元可在不涉及任何糖基化步骤的情况下，以灵活高效的方式组装，并且链可以向非还原端（6'-OH）或还原端（1-OH）延伸，便于合成脂磷酸甘露聚糖、蛋白磷酸甘露聚糖及其类似物。

  DOI：

  10.1039/b106634j
• 作为产物：
  描述：

  乙酸酐 、 6-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl-(1->4)-α-D-mannopyranose 在 吡啶 作用下， 反应 16.0h， 以99%的产率得到1,2,3,6-tetra-O-acetyl-4-O-[2,3,4-tri-O-acetyl-6-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose
  参考文献：
  名称：

  Efficient synthesis of the antigenic phosphoglycans of the Leishmania parasite

  摘要：

  利什曼原虫的抗原性磷酸甘露聚糖重复单元可在不涉及任何糖基化步骤的情况下，以灵活高效的方式组装，并且链可以向非还原端（6'-OH）或还原端（1-OH）延伸，便于合成脂磷酸甘露聚糖、蛋白磷酸甘露聚糖及其类似物。

  DOI：

  10.1039/b106634j

文献信息

• Iterative Synthesis of <i>Leishmania</i> Phosphoglycans by Solution, Solid-Phase, and Polycondensation Approaches without Involving Any Glycosylation
  作者：Dipali Ruhela、Ram A. Vishwakarma

  DOI：10.1021/jo0341867

  日期：2003.5.1

  A general strategy (solution, solid-phase, and polycondensation) for the synthesis of antigenic phosphoglycans (PG) of the protozoan parasite Leishmania is presented. Phosphoglycans constitute the variable structural and functional domain of major cell-surface lipophosphoglycan (LPG) and secreted proteophosphoglycan (PPG), the molecules involved in infectivity and survival of the Leishmania parasite inside human macrophages. We have shown that the chemically labile, anomerically phosphodiester-linked phosphoglycan repeats can be assembled in an iterative and efficient manner from a single key intermediate, without involving any glycosylation steps. Furthermore, the phosphoglycan chain can be extended toward either the nonreducing (6'-OH) or the reducing (1-OH) end. We also describe a new and efficient solid-phase methodology to construct phosphoglycans based on design and application of a novel cis-allylphosphoryl solid-phase linker that enabled the selective cleavage of the first anomeric-phosphodiester linkage without affecting any of the other internal anomeric-phosphodiester groups of the growing PG chain on the solid support. The strategy to construct larger phosphoglycans in a one-pot synthesis by polycondensation of a single key intermediate is also described, enabling CD spectrometric measurements to show the helical nature of phosphoglycans. Our versatile synthetic approach provides easy access to Leishmania phosphoglycans and the opportunity to address key immunological, biochemical, and biophysical questions pertaining to the phosphoglycan family (LPG and PPG) unique to the parasite.