Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2,2-bis-hexadecyloxymethyl-propoxy]-tetrahydro-pyran-4-yl ester | 194930-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2,2-bis-hexadecyloxymethyl-propoxy]-tetrahydro-pyran-4-yl ester
• CAS: 194930-74-0
• 化学式: C₆₅H₁₁₄N₂O₂₀
• 分子量: 1243.62
• InChiKey: MUQIRDINNHLBKK-UIMJOBGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.31
• 重原子数：
  87.0
• 可旋转键数：
  50.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  271.38
• 氢给体数：
  2.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2,2-bis-hexadecyloxymethyl-propoxy]-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以72%的产率得到N-{(2R,3R,4R,5S,6R)-2-[3-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2,2-bis-hexadecyloxymethyl-propoxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide
  参考文献：
  名称：

  Synthesis and interfacial behaviour of a gemini neoglycolipid

  摘要：

  A gemini neoglycolipid was synthetised from pentaerythritol as the central building block to which were coupled two lipid moieties (C16H33 alkyl chains). The subsequent glycosylation reaction with two carbohydrate units (beta-D-GlcNAc) was achieved in acceptable yields which were, nevertheless, much lower than those obtained with the single-chain homologous derivatives. The behaviour of this neoglycolipid in monolayer was studied in details after spreading at an air/water interface. These molecules exhibit transition phases when the monolayer is compressed, revealing a similar behaviour to that of phospholipids. The behaviour of neoglycolipid 1 suggests a peculiar conformation at the air/water interface. This supramolecular arrangement might be taken as a model for molecular recognition of glycolipids in organized systems. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00029-7
• 作为产物：
  描述：

  5,5-双(羟甲基)-2-苯基-1,3-二氧杂环己烷 在 palladium on activated charcoal sodium hydroxide 、 4 A molecular sieve 、 四丁基溴化铵 、 氢气 、 三氯化铁 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 47.0h， 生成 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2,2-bis-hexadecyloxymethyl-propoxy]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis and interfacial behaviour of a gemini neoglycolipid

  摘要：

  A gemini neoglycolipid was synthetised from pentaerythritol as the central building block to which were coupled two lipid moieties (C16H33 alkyl chains). The subsequent glycosylation reaction with two carbohydrate units (beta-D-GlcNAc) was achieved in acceptable yields which were, nevertheless, much lower than those obtained with the single-chain homologous derivatives. The behaviour of this neoglycolipid in monolayer was studied in details after spreading at an air/water interface. These molecules exhibit transition phases when the monolayer is compressed, revealing a similar behaviour to that of phospholipids. The behaviour of neoglycolipid 1 suggests a peculiar conformation at the air/water interface. This supramolecular arrangement might be taken as a model for molecular recognition of glycolipids in organized systems. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00029-7