6-desoxy-6-amino-1-O-(2,3-bis(octadecyloxy)propyl)-β-D-glucopyranoside | 1338832-65-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 6-desoxy-6-amino-1-O-(2,3-bis(octadecyloxy)propyl)-β-D-glucopyranoside
• CAS: 1338832-65-7
• 化学式: C₄₅H₉₁NO₇
• 分子量: 758.22
• InChiKey: MZCDDCLXRWRITK-XXDFPZRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.69
• 重原子数：
  53.0
• 可旋转键数：
  41.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  123.63
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-desoxy-6-amino-1-O-(2,3-bis(octadecyloxy)propyl)-β-D-glucopyranoside 、 D-生物素 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以61%的产率得到6-desoxy-6-biotinylamino-1-O-(2,3-bis(octadecyloxy)propyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel amphiphilic conjugates with a biological recognition function for developing targeted triggered liposomal delivery systems

  摘要：

  Several novel amphiphilic lipid derivatives were synthesized consisting of a lipid anchor connected to the hydrophilic moiety via a disulfide or glycoside bond and biotin linked to the hydrophilic part. Disulfide bonds were established by the help of 4-phenyltriazol-3,5-dione. Dansyl or fluorescein was covalently linked as fluorescent marker to some of the conjugates, allowing spectroscopic and microscopic detection. The conjugates represent first amphiphilic lipids carrying all four functions, i.e., lipophilic, hydrophilic, recognition, and disulfide cleavage group in one molecule, which are necessary for targeted, triggered drug delivery from phospholipid liposomes on demand. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.089
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 甲醇 、 氨 、 碘 、 sodium methylate 、 四丁基硫酸氢铵 、 silver carbonate 、 sodium hydroxide 、 silver(l) oxide 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 13.0~50.0 ℃ 、1.0 MPa 条件下， 反应 92.0h， 生成 6-desoxy-6-amino-1-O-(2,3-bis(octadecyloxy)propyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel amphiphilic conjugates with a biological recognition function for developing targeted triggered liposomal delivery systems

  摘要：

  Several novel amphiphilic lipid derivatives were synthesized consisting of a lipid anchor connected to the hydrophilic moiety via a disulfide or glycoside bond and biotin linked to the hydrophilic part. Disulfide bonds were established by the help of 4-phenyltriazol-3,5-dione. Dansyl or fluorescein was covalently linked as fluorescent marker to some of the conjugates, allowing spectroscopic and microscopic detection. The conjugates represent first amphiphilic lipids carrying all four functions, i.e., lipophilic, hydrophilic, recognition, and disulfide cleavage group in one molecule, which are necessary for targeted, triggered drug delivery from phospholipid liposomes on demand. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.089