1-O-(2,3-bis(octadecyloxy)propyl)-β-D-glucopyranoside | 85618-46-8

• 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: 1-O-(2,3-bis(octadecyloxy)propyl)-β-D-glucopyranoside
• 英文别名: 1,2-di-O-octadecyl-3-O-(β-D-glucopyranosyl)glycerol；dioctadecyl glycerylether-β-glucosides；(2R,3R,4S,5S,6R)-2-(2,3-dioctadecoxypropoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 85618-46-8
• 化学式: C₄₅H₉₀O₈
• 分子量: 759.205
• InChiKey: MFVNGXROPZZJTB-XXDFPZRJSA-N

物化性质

• 熔点：
  57-60 °C
• 沸点：
  797.0±60.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.4
• 重原子数：
  53
• 可旋转键数：
  41
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-O-(2,3-bis(octadecyloxy)propyl)-β-D-glucopyranoside 在 氨 、 四丁基硫酸氢铵 、 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 13.0~25.0 ℃ 、1.0 MPa 条件下， 反应 44.0h， 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
• 作为产物：
  描述：

  rac-1,2-di-O-octadecylglycerol 在 甲醇 、 碘 、 sodium methylate 、 silver carbonate 、 silver(l) oxide 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 48.0h， 生成 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

文献信息

• Alshoaibi; Morozova; Serebrennikova, Russian Journal of Bioorganic Chemistry, 2000, vol. 26, # 9, p. 633 - 636
  作者：Alshoaibi、Morozova、Serebrennikova

  DOI：——

  日期：——
• An efficient and stereoselective synthesis of 1,2-0-dialkyl-3-0-β-d-dlycosyl-sn-glycerols
  作者：Lambert Six、Klaus-Peter Rueβ、Manfred Liefländer

  DOI：10.1016/s0040-4039(00)81621-4

  日期：1983.1
• Synthesis of novel amphiphilic conjugates with a biological recognition function for developing targeted triggered liposomal delivery systems
  作者：Nicolai Brodersen、Anna Arbuzova、Andreas Herrmann、Holger Egger、Jürgen Liebscher

  DOI：10.1016/j.tet.2011.07.089

  日期：2011.10

  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.