1,3-bis(undecyloxy)propan-2-ol | 201995-24-6

• 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: 1,3-bis(undecyloxy)propan-2-ol
• 英文别名: 1,3-Bis(undecyloxy)propan-2-OL；1,3-di(undecoxy)propan-2-ol
• CAS: 201995-24-6
• 化学式: C₂₅H₅₂O₃
• 分子量: 400.686
• InChiKey: ZQCMZNFRIZWOJD-UHFFFAOYSA-N

物化性质

• 熔点：
  35 °C
• 沸点：
  490.8±30.0 °C(Predicted)
• 密度：
  0.886±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  28
• 可旋转键数：
  24
• 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(undecyloxy)propan-2-ol 在 盐酸 、 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 122.0h， 生成 2-O-(2-hydroxyethyl)-1,3-bis(undecyloxy)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
• 作为产物：
  描述：

  1-溴十一烷 在 盐酸 、 sodium hydroxide 、 二正丁基氧化锡 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 38.0h， 生成 1,3-bis(undecyloxy)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 l-glucosamine donors for 1,2-trans-glycosylation reactions
  作者：Dominique Lafont、Paul Boullanger

  DOI：10.1016/j.tetasy.2006.12.011

  日期：2006.12

  Two new L-glucosarnine donors, that is pent-4-enyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-beta-L-glucopyranoside 16 and ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-l-thio-beta-L-glucopyranoside 21 were prepared in 12 steps from L-arabinose. The reaction pathway uses 3,4,6-tri-O-acetyl-L-glucal 5, and then 3,4,6-tri-O-acetyl-2-deoxy-2-iodO-alpha-L-mannopyranosyl azide 8 as intermediates. The latter, together with donors 16 and 21, were used for preparing L-glucosamine neoglycolipids. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and interfacial behavior of three homologous glycero neoglycolipids with various chain lengths
  作者：P Boullanger、M.-R Sancho-Camborieux、M.-N Bouchu、L Marron-Brignone、R.M Morelis、P.R Coulet

  DOI：10.1016/s0009-3084(97)00076-5

  日期：1997.11

  Three neoglycolipids la-e derived from glycerol were synthezised and their molecular arrangements were studied at the air/water interface through Langmuir-Blodgett technique. The common structural features of these neoglycolipids are: a triethyleneglycol spacer at C-2 of glycerol, a GlcNAc hydrophilic head group at the end of the spacer, two saturated aliphatic chains at C-l and C-3 of glycerol, linked by ether bonds. Compounds la-e differ only by the length of their lipid moieties. By increasing the hydrocarbon chain length from C-11 to C-16, a densely packed state was reached in the monolayer. The compression isotherms displayed an expanded state during the whole compression for compounds la and Ic bearing two C-11 or one C-11 and one C-16 chains. Compound 1b bearing two C-16 chains displayed a quite different interfacial behavior. The transfer of these monolayers onto a solid substrate can be obtained only with a trigger molecule, a phosphatidic acid. (C) 1997 Elsevier Science Ireland Ltd.
• 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.