(R)-3-(octadecanoyloxy)icosanoic acid | 828939-44-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-3-(octadecanoyloxy)icosanoic acid
• 英文别名: (3R)-3-octadecanoyloxyicosanoic acid
• CAS: 828939-44-2
• 化学式: C₃₈H₇₄O₄
• 分子量: 595.003
• InChiKey: FZKDEYBMTFCURH-PSXMRANNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.9
• 重原子数：
  42
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-(octadecanoyloxy)icosanoic acid 、 allyl 6-O-{2-amino-6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-β-D-glucopyranosyl}-4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以86%的产率得到allyl 4-O-benzyl-6-O-{6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-2-[(R)-3-(octadecanoyloxy)icosanoylamino]-3-O-tetradecanoyl-β-D-glucopyranosyl}-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：

  3-氧代二十烷酸甲酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 [(S)-2,2'-双(二苯基磷)-1,1'-联萘]二氯化钌(II) 、 氢气 、 铜 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 20.0~60.0 ℃ 、8.61 MPa 条件下， 反应 73.0h， 生成 (R)-3-(octadecanoyloxy)icosanoic acid
  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

文献信息

• Synthesis and purity assessment of tetra- and pentaacyl lipid A of Chlamydia containing (R)-3-hydroxyicosanoic acid
  作者：Alla Zamyatina、Harald Sekljic、Helmut Brade、Paul Kosma

  DOI：10.1016/j.tet.2004.10.017

  日期：2004.12

  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.