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 | 909543-74-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 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
• CAS: 909543-74-4
• 化学式: C₄₄H₆₃ClO₂₆
• 分子量: 1043.42
• InChiKey: ORDCNNRHMJIUGB-LPURLQFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  71.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  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 作用下， 以 甲醇 为溶剂， 以96%的产率得到6-chlorohexyl 4-O-[4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl]-1-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：

  O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→4)-O-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.5h， 生成 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
  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