1,3,4,6-tetra-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranose | 76898-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranose
• CAS: 76898-73-2
• 化学式: C₂₈H₃₈O₁₉
• 分子量: 678.598
• InChiKey: RMIOUCGMUWKQRI-MQFIMZJJSA-N

物化性质

• 沸点：
  670.1±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  238.09
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranose 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以100%的产率得到
  参考文献：
  名称：

  Synthesis of Mucin Glycans from the Protozoon ParasiteTrypanosoma cruzi

  摘要：

  本研究报道了一种短程、顺时针、2+2-糖基化方法合成克氏锥虫粘蛋白的四糖成分。尽管使用了 1,2-链二糖供体，但在关键的糖基化步骤中实现了高产率（79%）和良好的立体控制（>10:1, δ²:δ）。初步研究表明，这种支链四糖可作为寄生虫细胞表面反式硅烷基化酶的底物。

  DOI：

  10.1055/s-2008-1078249
• 作为产物：
  描述：

  4-甲基苯基2,3,4,6-四-O-乙酰基-1-硫代吡喃己糖苷 在 N-碘代丁二酰亚胺 、 benzyl 3,5,6-tri-O-benzoyl-β-D-galactofuranosyl-(1→4)-2-acetamido-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranoside 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 22.08h， 以46%的产率得到1,3,4,6-tetra-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of the hexasaccharide from Trypanosoma cruzi mucins with the Galp(1 → 2)Galf unit constructed with a superarmed thiogalactopyranosyl donor

  摘要：

  Hexasaccharide beta-D-Galp-(1 -> 2)-[beta-D-Galp-(1 -> 3)]-beta-D-Galp-(1 -> 6)-[beta-D-Galp-(1 -> 2)-beta-D-Galf-(1 -> 4)]-D-GlcNAc (1) was found O-linked in mucins of Trypanosoma cruzi epimastigotes and metacyclic trypomatigotes. Studies on the biological pathways and functionalities of the mucin oligosaccharides are prompted in order to understand the interactions of these molecules with the insect host. Trisaccharide constituent beta-D-Galp-(1 -> 2)-beta-D-Galf-(1 -> 4)-D-GlcNAc was constructed from the reducing to the non-reducing end. We discuss the difficulties to introduce a Galp unit at the O-2 position of a partially protected galactofuranosyl unit which were overcome using an anchimerically superarmed donor. By this route and employing a [3 + 3] nitrilium convergent approach hexasaccharide 1 was synthesized in moderate yield.

  DOI：

  10.1016/j.carres.2019.06.013

文献信息

• Mass spectra of peracetates of some (1→2)-linked disaccharides
  作者：Tsuyoshi Fujiwara、Kiyoshi Arai

  DOI：10.1016/s0008-6215(00)85186-1

  日期：1980.12

  Abstract The mass spectra of two peracetylated disaccharides and the pentaacetate ( 1 ) of an aldobiouronic acid methyl ester, all having a (1→2)-linkage, were analyzed. The fragmentation pathway common to these compounds could be classified into four groups: ( 1 ) the aA type, which was the main pathway, ( 2 ) the abJ type, ( 3 ) the baA type, and ( 4 ) the baC type. The manner of fragmentation of

  摘要分析了均具有（1→2）键的两个过乙酰化二糖和醛双糖醛酸甲酯的五乙酸盐（1）的质谱。这些化合物共有的裂解途径可分为四类：（1）aA型是主要途径，（2）abJ型，（3）baA型，以及（4）baC型。过乙酸盐1的断裂方式与二糖类似。
• Reactivity of sugar trityl ethers in trityl?cyanoalkylidene condensation
  作者：P. I. Kitov、Yu. E. Tsvetkov、L. V. Backinowsky、N. K. Kochetkov

  DOI：10.1007/bf00699016

  日期：1993.11

  The reactivity of a series of primary and secondary sugar trityl ethers in trityl-cyanoalkylidene condensation has been determined. It was found that the stereoselectivity of glycosylation by this method does not directly depend on the reactivity of the trityl ethers. Based on the results obtained, a stepwise mechanism rather than a concerted mechanism has been chosen as the most probable.