allyl 2-amino-4-O-benzyl-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside | 828939-74-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: allyl 2-amino-4-O-benzyl-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-amino-2-(hydroxymethyl)-3-phenylmethoxy-6-prop-2-enoxyoxan-4-yl] tetradecanoate
• CAS: 828939-74-8
• 化学式: C₃₀H₄₉NO₆
• 分子量: 519.722
• InChiKey: BRJYZKMPJWOWTE-JXQOEZKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  37
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-3-(benzyloxy)icosanoic acid 、 allyl 2-amino-4-O-benzyl-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 1.0h， 以85%的产率得到allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and purity assessment of tetra- and pentaacyl lipid A of Chlamydia containing (R)-3-hydroxyicosanoic acid

  摘要：

  Based on structural data of lipid A from Chlamydia trachomatis strains, chemically pure tetra- and pentaacyl 1,4'-bisphosphoryl as well as the related 4'-monophosphoryl derivatives of lipid A were synthesized. (R)-3-Hydroxyicosanoic acid as a chiral constituent was prepared via Noyori-reduction of methyl-3-oxoicosanoic acid. Synthetic intermediates were O-acylated with myristoic acid residues at positions 3 and 3' and N-acylated with (R)-3-hydroxyicosanoic acid at both glucosamine units. Efficient purification methods for highly hydrophobic long-chain tri-, tetra- and pentaacyl progenitors of lipid A have been developed. Purity and homogeneity of the synthetic target compounds were confirmed by NMR and MS-data as well as a sensitive immunostaining approach. The tetra- and pentaacyl species serve as biomedical probes to investigate the endotoxic potential of chlamydial lipid A and to clarify its role in Chlamydia associated infections. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.017
• 作为产物：
  描述：

  allyl 4-O-benzyl-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 在 溶剂黄146 、 锌 作用下， 反应 4.0h， 以89%的产率得到allyl 2-amino-4-O-benzyl-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and purity assessment of tetra- and pentaacyl lipid A of Chlamydia containing (R)-3-hydroxyicosanoic acid

  摘要：

  Based on structural data of lipid A from Chlamydia trachomatis strains, chemically pure tetra- and pentaacyl 1,4'-bisphosphoryl as well as the related 4'-monophosphoryl derivatives of lipid A were synthesized. (R)-3-Hydroxyicosanoic acid as a chiral constituent was prepared via Noyori-reduction of methyl-3-oxoicosanoic acid. Synthetic intermediates were O-acylated with myristoic acid residues at positions 3 and 3' and N-acylated with (R)-3-hydroxyicosanoic acid at both glucosamine units. Efficient purification methods for highly hydrophobic long-chain tri-, tetra- and pentaacyl progenitors of lipid A have been developed. Purity and homogeneity of the synthetic target compounds were confirmed by NMR and MS-data as well as a sensitive immunostaining approach. The tetra- and pentaacyl species serve as biomedical probes to investigate the endotoxic potential of chlamydial lipid A and to clarify its role in Chlamydia associated infections. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.017