N-tetradecanoyl-O-<6-O-benzyloxymethyl-2-deoxy-4-O-diphenylphosphono-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-serine benzyl ester | 155711-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-tetradecanoyl-O-<6-O-benzyloxymethyl-2-deoxy-4-O-diphenylphosphono-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-serine benzyl ester
• 英文别名: [(2R,3R,4R,5S,6R)-5-diphenoxyphosphoryloxy-2-[(2S)-3-oxo-3-phenylmethoxy-2-(tetradecanoylamino)propoxy]-6-(phenylmethoxymethoxymethyl)-3-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]oxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 155711-42-5
• 化学式: C₁₀₆H₁₇₁N₂O₁₈P
• 分子量: 1792.5
• InChiKey: MTDBKEQQUYQYEN-XXKXKCFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  34
• 重原子数：
  127
• 可旋转键数：
  87
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  245
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  N-tetradecanoyl-O-<6-O-benzyloxymethyl-2-deoxy-4-O-diphenylphosphono-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-serine benzyl ester 在 palladium on activated charcoal platinum(IV) oxide 、 氢气 作用下， 生成 (R)-3-Tetradecanoyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-((S)-2-carboxy-2-tetradecanoylamino-ethoxy)-5-(diphenoxy-phosphoryloxy)-6-hydroxymethyl-3-((R)-3-tetradecanoyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Lipid A and Related Compounds. XXVIIII, Part XXVIII: Synthesis of Biologically Active N-Acylated L-Serine-Containing D-Glucosamine-4-phosphate Derivatives of Lipid A.

  摘要：

  合成了新的N-酰基化的L-丝氨酸非磷酸化和磷酸化的D-氨基葡萄糖衍生物，这些化合物在结构上对应于脂质A二糖骨架。化合物4和5显示出促细胞增殖活性。

  DOI：

  10.1248/cpb.41.1879
• 作为产物：
  描述：

  (R)-3-(dodecanoyloxy)tetradecanoic acid 、 benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-amino-5-diphenoxyphosphoryloxy-4-hydroxy-6-(phenylmethoxymethoxymethyl)oxan-2-yl]oxy-2-(tetradecanoylamino)propanoate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以56%的产率得到N-tetradecanoyl-O-<6-O-benzyloxymethyl-2-deoxy-4-O-diphenylphosphono-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-serine benzyl ester
  参考文献：
  名称：

  Lipid A and Related Compounds. XXVIIII, Part XXVIII: Synthesis of Biologically Active N-Acylated L-Serine-Containing D-Glucosamine-4-phosphate Derivatives of Lipid A.

  摘要：

  合成了新的N-酰基化的L-丝氨酸非磷酸化和磷酸化的D-氨基葡萄糖衍生物，这些化合物在结构上对应于脂质A二糖骨架。化合物4和5显示出促细胞增殖活性。

  DOI：

  10.1248/cpb.41.1879

文献信息

• Lipid A and Related Compounds. XXXI. Synthesis of Biologically Active N-Acylated L-Serine-Containing D-Glucosamine 4-Phosphate Derivatives of Lipid A.
  作者：Keisuke MIYAJIMA、Kiyoshi IKEDA、Kazuo ACHIWA

  DOI：10.1248/cpb.44.2268

  日期：——

  New N-acylated L-serine-containing non-phosphorylated and phosphorylated D-glucosamine derivatives structurally corresponding to the lipid A disaccharide backbone were synthesized. Compounds 2, 4 and 5 exhibited potent mitogenic activity. Further, compound 5 showed nitric oxide (NO) productivity.

  合成了新的N-酰化L-丝氨酸含非磷酸化和磷酸化的D-葡萄糖胺衍生物，这些衍生物在结构上对应脂质A二糖骨架。化合物2、4和5表现出强烈的促分裂活性。此外，化合物5显示出一氧化氮（NO）的产生能力。