4-bromophenyl (2,3,4,6-tetra-O-acetyl-β-D-glucoyranosyl)-(1-4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside | 215775-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-bromophenyl (2,3,4,6-tetra-O-acetyl-β-D-glucoyranosyl)-(1-4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 215775-96-5
• 化学式: C₄₄H₅₅BrO₂₆
• 分子量: 1079.81
• InChiKey: FKOLEJLEYYELPF-GYZWJJPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  71.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  318.38
• 氢给体数：
  0.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  4-bromophenyl (2,3,4,6-tetra-O-acetyl-β-D-glucoyranosyl)-(1-4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 4-bromophenyl β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-3)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of aryl 3-O-β-cellobiosyl-β-d-glucopyranosides for reactivity studies of 1,3-1,4-β-glucanases

  摘要：

  A series of substituted aryl beta-glycosides derived from 3-O-beta-cellobiosyl-D-glucopyranose with different phenol-leaving group abilities as measured by the pK(a) of the free phenol group upon enzymatic hydrolysis has been synthesised. Aryl beta-glycosides with a pK(a) of the free phenol leaving group > 5 were prepared by phase-transfer glycosidation of the per-O-acetylated alpha-glycosyl bromide with the corresponding phenol, whereas the 2,4-dinitrophenyl beta-glycoside was obtained by condensation of 1-fluoro-2,4-dinitrobenzene with the partially acetylated trisaccharide followed by acid de-O-acetylation. The aryl beta-glycosides have been used for reactivity studies of the wild-type Bacillus licheniformis 1,3-1,4-beta-D-glucan 4-glucanohydrolase. The Hammett plot log k(cat) versus pK(a) is biphasic with an upward curvature at low pK(a) values suggesting a change in transition-state structure depending on the aglycon. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00175-x
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-acetyl-β-D-glucoyranosyl)-(1-4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-3)-1,2,4,6-tetra-O-acetyl-D-glucopyranose 在 sodium hydroxide 、 氢溴酸 、 苄基三乙基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 4-bromophenyl (2,3,4,6-tetra-O-acetyl-β-D-glucoyranosyl)-(1-4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of aryl 3-O-β-cellobiosyl-β-d-glucopyranosides for reactivity studies of 1,3-1,4-β-glucanases

  摘要：

  A series of substituted aryl beta-glycosides derived from 3-O-beta-cellobiosyl-D-glucopyranose with different phenol-leaving group abilities as measured by the pK(a) of the free phenol group upon enzymatic hydrolysis has been synthesised. Aryl beta-glycosides with a pK(a) of the free phenol leaving group > 5 were prepared by phase-transfer glycosidation of the per-O-acetylated alpha-glycosyl bromide with the corresponding phenol, whereas the 2,4-dinitrophenyl beta-glycoside was obtained by condensation of 1-fluoro-2,4-dinitrobenzene with the partially acetylated trisaccharide followed by acid de-O-acetylation. The aryl beta-glycosides have been used for reactivity studies of the wild-type Bacillus licheniformis 1,3-1,4-beta-D-glucan 4-glucanohydrolase. The Hammett plot log k(cat) versus pK(a) is biphasic with an upward curvature at low pK(a) values suggesting a change in transition-state structure depending on the aglycon. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00175-x