6-chlorohexyl 4-O-[4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl]-1-β-D-glucopyranoside | 909543-75-5

• 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-chlorohexyl 4-O-[4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl]-1-β-D-glucopyranoside
• CAS: 909543-75-5
• 化学式: C₂₄H₄₃ClO₁₆
• 分子量: 623.049
• InChiKey: ZAWOLWBVDJBDJM-SYGKRDOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.75
• 重原子数：
  41.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  257.68
• 氢给体数：
  10.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  6-chlorohexyl 4-O-[4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl]-1-β-D-glucopyranoside 、 (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以53%的产率得到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
• 作为产物：
  描述：

  O-[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-α-D-glucopyranosyl]trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.5h， 生成 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

文献信息

• Low-Concentration 1,2-<i>trans</i>β-Selective Glycosylation Strategy and Its Applications in Oligosaccharide Synthesis
  作者：Chin-Sheng Chao、Chen-Wei Li、Min-Chun Chen、Shih-Sheng Chang、Kwok-Kong Tony Mong

  DOI：10.1002/chem.200901119

  日期：2009.10.19

  This study develops an operationally easy, efficient, and general 1,2‐trans β‐selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent β‐selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of

  这项研究开发了一种易于操作，有效且通用的1,2-反式β-选择性糖基化反应，该反应在没有C2酰基功能的情况下进行。该过程采用化学上稳定的硫糖基供体和低底物浓度，以在糖基化反应中实现出色的β选择性。该方法可广泛应用于各种糖基底物，无论其结构和羟基保护功能如何。碳水化合物化学中这种低浓度的1,2-反式β-选择性糖基化消除了使用高反应性硫糖苷构建1,2-反式的限制β糖苷键。这有利于寡糖合成新策略的设计，如生物学相关的β-（1→6）-葡聚糖三糖，β-连接的Gb 3和isoGb 3衍生物的制备所示。