benzyl (2-O-(R)-10-methyloctadecanoyl-1-O-hexadecanoyl-sn-glycero)-diisopropylphosphoramidite | 935852-35-0

• 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: benzyl (2-O-(R)-10-methyloctadecanoyl-1-O-hexadecanoyl-sn-glycero)-diisopropylphosphoramidite
• 英文别名: [(2R)-1-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxy-3-hexadecanoyloxypropan-2-yl] (10R)-10-methyloctadecanoate
• CAS: 935852-35-0
• 化学式: C₅₁H₉₄NO₆P
• 分子量: 848.284
• InChiKey: FKTWWBIZJQFGFT-PTWBCSGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.2
• 重原子数：
  59
• 可旋转键数：
  44
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (2-O-(R)-10-methyloctadecanoyl-1-O-hexadecanoyl-sn-glycero)-diisopropylphosphoramidite 、 3,4,5,6-tetra-O-benzyl-2-O-(2',3',4',6'-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Synthesis and Structure of Phosphatidylinositol Dimannoside

  摘要：

  (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (S)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl)phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.

  DOI：

  10.1021/jo0625599
• 作为产物：
  描述：

  (10R)-1-benzyloxy-10-methyloctadecan-7-ol 在 palladium on activated charcoal 吡啶 、 四氮唑 、 4-二甲氨基吡啶 、 aluminum oxide 、 potassium permanganate 、 四丁基溴化铵 、 氢气 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 168.0h， 生成 benzyl (2-O-(R)-10-methyloctadecanoyl-1-O-hexadecanoyl-sn-glycero)-diisopropylphosphoramidite
  参考文献：
  名称：

  Synthesis and Structure of Phosphatidylinositol Dimannoside

  摘要：

  (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (S)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl)phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.

  DOI：

  10.1021/jo0625599