2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranose | 1256734-02-7

• 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-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranose
• 英文别名: Hepta-O-acetyl-α-gentiobiose；Glc2Ac3Ac4Ac6Ac(b1-6)a-Glc2Ac3Ac4Ac；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-hydroxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 1256734-02-7
• 化学式: C₂₆H₃₆O₁₈
• 分子量: 636.561
• InChiKey: SPWFGEAKPYYJQD-DEZPWFOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  232
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  1,2,3,4,2',3',4',6'-octa-O-acetylgentiobiose 在 溶剂黄146 、 乙二胺 作用下， 以 四氢呋喃 为溶剂， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranose 、 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  An Alternative Method for Regioselective, Anomeric Deacylation of Fully Acylated Carbohydrates

  摘要：

  Ethylenediamine in admixture with acetic acid has been found useful to selectively effect the title conversion and can be of general utility. Reaction rates anomeric deacylations effected with this reagent are slower than with reagents introduced earlier, resulting in easier control and greater selectivity of deprotection.

  DOI：

  10.1080/07328309908544010

文献信息

• Synthesis of 5-O-oligoglucosyl extended α-(2→4)-Kdo disaccharides corresponding to inner core fragments of Moraxellaceae lipopolysaccharides
  作者：Barbara Pokorny、Paul Kosma

  DOI：10.1016/j.carres.2015.12.009

  日期：2016.3

  The heptose-deficient inner core of the lipopolysaccharide of several pathogenic strains of the Moraxellaceae family (Moraxella, Acinetobacter) and of Bartonella henselae, respectively, comprises an α-D-glucopyranose attached to position 5 of Kdo. In continuation of the synthesis of fragments of Acinetobacter haemolyticus LPS, the branched α-Glcp-(1 → 5)[α-Kdo-(2 → 4)]-α-Kdo trisaccharide motif was

  莫拉氏菌科（Moraxella，不动杆菌）和汉氏巴尔通体的数种致病菌株的脂多糖的庚糖缺陷的内核分别包含附着于Kdo 5位的α-D-吡喃葡萄糖。为了继续合成溶血不动杆菌LPS的片段，精心设计了分支的α-Glcp-（1→5）[α-Kdo-（2→4）]-α-Kdo三糖基序。使用4,6-O-亚苄基N-苯基三氟乙酰亚氨基葡糖基供体，可以高收率和公平的端基选择性实现适当保护的，α-（2→4）交联的Kdo-二糖的糖基化作用。随后的区域选择性还原性亚苄基打开提供了三糖受体，其被β-D-吡喃葡萄糖基和异麦芽糖基残基所扩展。