8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside | 890049-63-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
• CAS: 890049-63-5
• 化学式: C₄₆H₇₁N₃O₈
• 分子量: 794.085
• InChiKey: PLBFTPOAAAABEO-BCNLBKMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.34
• 重原子数：
  57.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  133.6
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三氟化硼乙醚 、 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-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：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 34.0h， 生成 8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctyl 2-azido-4,6-O-benzylidene-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