allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside | 828939-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-2-(hydroxymethyl)-3-phenylmethoxy-5-[[(3R)-3-phenylmethoxyicosanoyl]amino]-6-prop-2-enoxyoxan-4-yl] tetradecanoate
• CAS: 828939-76-0
• 化学式: C₅₇H₉₃NO₈
• 分子量: 920.367
• InChiKey: LSSOAZSNKPDATE-BEQLEUCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  66
• 可旋转键数：
  43
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate 、 allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以93%的产率得到allyl 4-O-benzyl-6-O-{6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-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 三乙基硅烷 、 lithium hydroxide 、 [(S)-2,2'-双(二苯基磷)-1,1'-联萘]二氯化钌(II) 、 六甲基二硅氧烷 、 三氟甲磺酸三甲基硅酯 、 氢气 、 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 60.0 ℃ 、8.61 MPa 条件下， 反应 48.0h， 生成 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

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.