5-(4-allyloxyphenyl)-3-oxapentyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside | 1061303-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-allyloxyphenyl)-3-oxapentyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside
• CAS: 1061303-00-1
• 化学式: C₄₇H₅₂O₈
• 分子量: 744.925
• InChiKey: DENKXNRWGLWWFO-ABOIGXJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.53
• 重原子数：
  55.0
• 可旋转键数：
  23.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-(4-allyloxyphenyl)-3-oxapentyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 在 9-硼双环[3.3.1]壬烷 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以96%的产率得到5-[4-(3-hydroxypropyloxy)phenyl]-3-oxapentyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Design, synthesis and evaluation of d-galactose-β-cyclodextrin conjugates as drug-carrying molecules

  摘要：

  Several kinds of D-galactose-beta-cyclodextrin conjugates having a phenyl group in the spacers between the D-galactose and beta-cyclodextrin were designed and synthesized as drug-carrying molecules. Their evaluation as drug-carrying molecules was done by measuring the molecular interactions with the anticancer agent, doxorubicin, and with the D-galactose-binding peanut lectin using an SPR optical biosensor. The SPR analyses showed that these conjugates had remarkably high inclusion associations of 10(5) similar to 10(7) M-1 levels for the immobilized doxorubicin. Their association constants for immobilized peanut lectin were at the level of 10(4) similar to 10(5) M-1, as we expected. These conjugates will be useful drug-carrying models which can site-specifically carry doxorubicin to the cells containing D-galactose-binding lectin. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.076
• 作为产物：
  描述：

  5-(4-allyloxyphenyl)-3-oxapentyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 、 溴甲苯 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 以84%的产率得到5-(4-allyloxyphenyl)-3-oxapentyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Design, synthesis and evaluation of d-galactose-β-cyclodextrin conjugates as drug-carrying molecules

  摘要：

  Several kinds of D-galactose-beta-cyclodextrin conjugates having a phenyl group in the spacers between the D-galactose and beta-cyclodextrin were designed and synthesized as drug-carrying molecules. Their evaluation as drug-carrying molecules was done by measuring the molecular interactions with the anticancer agent, doxorubicin, and with the D-galactose-binding peanut lectin using an SPR optical biosensor. The SPR analyses showed that these conjugates had remarkably high inclusion associations of 10(5) similar to 10(7) M-1 levels for the immobilized doxorubicin. Their association constants for immobilized peanut lectin were at the level of 10(4) similar to 10(5) M-1, as we expected. These conjugates will be useful drug-carrying models which can site-specifically carry doxorubicin to the cells containing D-galactose-binding lectin. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.076