4-undecyloxymethyl-3,6-dioxaheptadecyl O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serinamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-undecyloxymethyl-3,6-dioxaheptadecyl O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serinamide
• 英文别名: (2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-amino-N-[2-[1,3-di(undecoxy)propan-2-yloxy]ethyl]propanamide
• 化学式: C₃₈H₇₅N₃O₁₀
• 分子量: 734.028
• InChiKey: BJVZLWBNYBKOQS-OWRFXFELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  51
• 可旋转键数：
  34
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  191
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1-溴十一烷 在 palladium on activated charcoal 吗啉 、 盐酸 、 sodium hydroxide 、 氢气 、 sodium 、 sodium hydride 、 二正丁基氧化锡 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， -20.0~80.0 ℃ 、1.01 MPa 条件下， 反应 62.75h， 生成 4-undecyloxymethyl-3,6-dioxaheptadecyl O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serinamide
  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.