p-methoxyphenyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-6-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₅H₃₈O₁₇
• 分子量: 610.567
• InChiKey: SADQXSYAYSUILX-VAAZCZNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  267
• 氢给体数：
  10
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 2.0h， 以93%的产率得到4-methoxyphenyl 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-β-D-glucopyranoside
  参考文献：
  名称：

  Silicon nitride sugar chips for detection of Ricinus communis proteins and Escherichia coli O157 Shiga toxins

  摘要：

  Lactosides having either an amino-triethylene glycol or an azido-triethylene glycol were designed and synthesized, and the two derivatives were immobilized onto silicon nitride (SiN) surfaces. When a click reaction was applied for the immobilization of the azido-sugar, a Ricinus commons lectin (RCA(120)) was detected with a higher response by reflectometric interference spectroscopy (RIfS). When an N-hydroxysuccinimide (NHS) method was applied for the sugar immobilization, the response was less than that of the click one. The response of bovine serum albumin (BSA) as the negative control was negligible, but the lactose-SiN chip prepared by the click method suppressed nonspecific binding more effectively than did the chip from the NHS method. Next, we examined an antibody-immobilized SiN chip prepared by the click reaction. The detection response was, however, lower than that of the lactose-SiN chip, meaning that the sugar-chip by the click reaction was superior to the antibody-chip. Finally, to detect Shiga toxins from Escherichia coli O157:H7, globotrisaccharide (Gb(3)) with an azido-triethylene glycol was synthesized and immobilized onto the SiN chip by the click reaction. The Gb(3)-SiN chips enabled us to detect the toxins at concentrations less than 100 ng/mL. RCA(120), horse gram, gorse lectins and BSA showed no response to the Gb(3)-SiN chip, showing a high specificity for the toxin.

  DOI：

  10.1016/j.ab.2019.06.002
• 作为产物：
  描述：

  p-methoxyphenyl 4,6-di-O-acetyl-2-O-benzoyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 氨 作用下， 以 甲醇 为溶剂， 反应 168000.0h， 以86%的产率得到p-methoxyphenyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  A concise and practical synthesis of antigenic globotriose, α-d-Gal-(1→4)-β-d-Gal-(1→4)-β-d-Glc

  摘要：

  A concise and practical synthesis of the antigenic globotriose, alpha-D-Gal-(1 -> 4)-beta-D-Gal-(1 -> 4)-beta-D-Glc (13), was achieved by coupling of a monosaccharide donor, 3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-alpha-D-galactopyranosyl trichloroacetimidate (4) with a disaccharide acceptor, p-methoxyphenyl 2,3,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside (8), followed by deprotection. In spite of the existence of a C-2-ester substituent capable of neighboring-group participation in the donor, the coupling gave exclusively the alpha-linkage in satisfactory yield. The acceptor 8 was readily obtained from selective 3-O-benzoylation of the galactosyl. ring of p-methoxyphenyl 2,6-di-O-benzoyl-beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside (7), which was prepared from p-methoxyphenyl beta-D-lactoside (5) via isopropylidenation, benzoylation, and deisopropylidenation. Donor 4 was obtained from p-methoxylphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside (1) via selective 4,6-di-O-debenzoylation, oxidative removal of 1-O-MP, benzylidenation, and trichloroacetimidate formation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.029