6-(4-cinnamoylphenoxy)-hexyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 909543-67-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(4-cinnamoylphenoxy)-hexyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: (E)-1-[4-[6-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexoxy]phenyl]-3-phenylprop-2-en-1-one
• CAS: 909543-67-5
• 化学式: C₃₉H₅₄O₁₈
• 分子量: 810.847
• InChiKey: HYRBYWMHYJSAFY-KXNGDBFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  57
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  284
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  6-(4-cinnamoylphenoxy)-hexyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 、 乙酸酐 在 吡啶 作用下， 反应 48.0h， 以88%的产率得到6-(4-cinnamoylphenoxy)-hexyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel electrophilic thiol-specific carbohydrate reagents

  摘要：

  The galactosyl donor, 4,6-di-O-acetyl-2,3-di-O-benzyl-D-galactopyranosyl trichloroacetimidate, was efficiently coupled with regioselectively benzylated lactoside acceptors under standard conditions to stereoselectively afford the corresponding globotrioside and isoglobotrioside derivatives in very good yields. These glycosides were smoothly functionalized with a 6-(p-cinnamoylplienoxy)-hexyl tether tag as novel electrophilic thiol-specific carbohydrate reagents. Immobilization of the globotrioside conjugate to Thiopropyl Sepharose 6B for purification of B-subunit of Shiga toxin (StxB) and coupling of a model cysteine-containing protein (StxB-Z(n)-Cys) to the isoglobotrioside conjugate were both performed with high efficiency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.044
• 作为产物：
  描述：

  6-chloro-n-hexyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 6-(4-cinnamoylphenoxy)-hexyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel electrophilic thiol-specific carbohydrate reagents

  摘要：

  The galactosyl donor, 4,6-di-O-acetyl-2,3-di-O-benzyl-D-galactopyranosyl trichloroacetimidate, was efficiently coupled with regioselectively benzylated lactoside acceptors under standard conditions to stereoselectively afford the corresponding globotrioside and isoglobotrioside derivatives in very good yields. These glycosides were smoothly functionalized with a 6-(p-cinnamoylplienoxy)-hexyl tether tag as novel electrophilic thiol-specific carbohydrate reagents. Immobilization of the globotrioside conjugate to Thiopropyl Sepharose 6B for purification of B-subunit of Shiga toxin (StxB) and coupling of a model cysteine-containing protein (StxB-Z(n)-Cys) to the isoglobotrioside conjugate were both performed with high efficiency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.044

文献信息

• Synthesis of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel electrophilic thiol-specific carbohydrate reagents
  作者：Mohamed R.E. Aly、Pascal Rochaix、Mohamed Amessou、Ludger Johannes、Jean-Claude Florent

  DOI：10.1016/j.carres.2006.03.044

  日期：2006.9

  The galactosyl donor, 4,6-di-O-acetyl-2,3-di-O-benzyl-D-galactopyranosyl trichloroacetimidate, was efficiently coupled with regioselectively benzylated lactoside acceptors under standard conditions to stereoselectively afford the corresponding globotrioside and isoglobotrioside derivatives in very good yields. These glycosides were smoothly functionalized with a 6-(p-cinnamoylplienoxy)-hexyl tether tag as novel electrophilic thiol-specific carbohydrate reagents. Immobilization of the globotrioside conjugate to Thiopropyl Sepharose 6B for purification of B-subunit of Shiga toxin (StxB) and coupling of a model cysteine-containing protein (StxB-Z(n)-Cys) to the isoglobotrioside conjugate were both performed with high efficiency. (c) 2006 Elsevier Ltd. All rights reserved.