1,3-bis(3,7,11,15-tetramethylhexadecyloxy)propan-2-ol | 103023-52-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,3-bis(3,7,11,15-tetramethylhexadecyloxy)propan-2-ol
• 英文别名: 1,3-Bis[(3,7,11,15-tetramethylhexadecyl)oxy]propan-2-OL；1,3-bis(3,7,11,15-tetramethylhexadecoxy)propan-2-ol
• CAS: 103023-52-5
• 化学式: C₄₃H₈₈O₃
• 分子量: 653.17
• InChiKey: IUIJIMKVPABOGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.2
• 重原子数：
  46
• 可旋转键数：
  34
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bis(3,7,11,15-tetramethylhexadecyloxy)propan-2-ol 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 64.75h， 生成 15,19,23,27-tetramethyl-10-(3,7,11,15-tetramethylhexadecyloxymethyl)-3,6,9,12-tetraoxaoctacosyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Syntheses of α-d-galactosamine neoglycolipids

  摘要：

  Several N-acetyl-alpha-D-galactosamine neoglycolipids, as well as hydrophobized T and T-N antigen analogues, were prepared for embedment onto liposomes. Three different lipidic structures were used for the anchoring, that is cholesterol, 1,3-bis(undecyloxy)propan-2-ol and 1, 3-bis(3,7,11,15-tetramethyl hexadecyloxy) propan-2-ol. Oligoethyleneglycol spacers were used to link the carbohydrate and the hydrophobic moieties; their lengths were varied in order to obtain model compounds for the selective recognition by sialyl transferases involved in cancer processes. Glycosylation reactions were optimized to sluggish amphiphilic acceptor alcohols, in order to reach good 1,2-cis-stereoselectivities and acceptable yields. This aim was achieved by using 3,4,6-tri-O-acetyl-2-azido-2deoxy-D-galactopyranosyl trichloroacetimidate as the donor, trimethylsilyl trifluoromethanesulfonate as the promoter and diethyl ether or mixtures of diethyl ether and dichloromethane as solvents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.013
• 作为产物：
  描述：

  叶绿醇 在 六甲基磷酰三胺 、 platinum(IV) oxide 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 20.0 ℃ 、405.3 kPa 条件下， 反应 23.0h， 生成 1,3-bis(3,7,11,15-tetramethylhexadecyloxy)propan-2-ol
  参考文献：
  名称：

  Syntheses of α-d-galactosamine neoglycolipids

  摘要：

  Several N-acetyl-alpha-D-galactosamine neoglycolipids, as well as hydrophobized T and T-N antigen analogues, were prepared for embedment onto liposomes. Three different lipidic structures were used for the anchoring, that is cholesterol, 1,3-bis(undecyloxy)propan-2-ol and 1, 3-bis(3,7,11,15-tetramethyl hexadecyloxy) propan-2-ol. Oligoethyleneglycol spacers were used to link the carbohydrate and the hydrophobic moieties; their lengths were varied in order to obtain model compounds for the selective recognition by sialyl transferases involved in cancer processes. Glycosylation reactions were optimized to sluggish amphiphilic acceptor alcohols, in order to reach good 1,2-cis-stereoselectivities and acceptable yields. This aim was achieved by using 3,4,6-tri-O-acetyl-2-azido-2deoxy-D-galactopyranosyl trichloroacetimidate as the donor, trimethylsilyl trifluoromethanesulfonate as the promoter and diethyl ether or mixtures of diethyl ether and dichloromethane as solvents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.013

文献信息

• Syntheses of α-d-galactosamine neoglycolipids
  作者：Nicolas Laurent、Dominique Lafont、Paul Boullanger

  DOI：10.1016/j.carres.2006.02.013

  日期：2006.5

  Several N-acetyl-alpha-D-galactosamine neoglycolipids, as well as hydrophobized T and T-N antigen analogues, were prepared for embedment onto liposomes. Three different lipidic structures were used for the anchoring, that is cholesterol, 1,3-bis(undecyloxy)propan-2-ol and 1, 3-bis(3,7,11,15-tetramethyl hexadecyloxy) propan-2-ol. Oligoethyleneglycol spacers were used to link the carbohydrate and the hydrophobic moieties; their lengths were varied in order to obtain model compounds for the selective recognition by sialyl transferases involved in cancer processes. Glycosylation reactions were optimized to sluggish amphiphilic acceptor alcohols, in order to reach good 1,2-cis-stereoselectivities and acceptable yields. This aim was achieved by using 3,4,6-tri-O-acetyl-2-azido-2deoxy-D-galactopyranosyl trichloroacetimidate as the donor, trimethylsilyl trifluoromethanesulfonate as the promoter and diethyl ether or mixtures of diethyl ether and dichloromethane as solvents. (c) 2006 Elsevier Ltd. All rights reserved.