(2S,3S,4R)-2-[(R)-2-hydroxytetracosanoylamino]-1,3,4-hexadecanetriol | 128802-67-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3S,4R)-2-[(R)-2-hydroxytetracosanoylamino]-1,3,4-hexadecanetriol
• 英文别名: (2S,3S,4R,2'R)-2-(2'-hydroxytetracosanoylamino)hexadecane-1,3,4-triol；(2R)-2-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyhexadecan-2-yl]tetracosanamide
• CAS: 128802-67-5
• 化学式: C₄₀H₈₁NO₅
• 分子量: 656.087
• InChiKey: WTMDDFOEGCODKM-KSLZXYGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  46
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-[(R)-2-hydroxytetracosanoylamino]-1,3,4-hexadecanetriol 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 2.0h， 生成 (2S,3R,4R)-2-((R)-2-(benzoyloxy)tetracosanamido)-1-(trityloxy)hexadecane-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis of a Hematoside Analog Containing Phytosphingosine and α-Hydroxyfatty Acid

  摘要：

  The hematoside analog 1 [NeuGc alpha(2-->3)Gal beta(1-->4)Glc beta(1-->1)Cer], which contains a phytosphingosine as a sphingoid base and an alpha-hydroxyfatty acid, has been synthesized. Coupling of the methyl (methyl 5-benzyloxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-alpha- and -beta-D-galacto-2-nonulopyranosid)onate 5, prepared from the corresponding 5-acetamido derivative 2, with a lactose derivative 6 afforded sialolactoside 7, which was converted to the corresponding trichloroacetimidate 10. Glycosylation of 10 with the ceramide tribenzoate 12 gave the protected hematoside analog 13, which was deprotected to the hematoside analog 1.

  DOI：

  10.1080/07328309708006548
• 作为产物：
  描述：

  (2S,3S,4R)-2-amino-1,3,4-hexadecanetriol 在 N-乙基吗啉 、 二甲基硫 、 B₃*Et₂O 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (2S,3S,4R)-2-[(R)-2-hydroxytetracosanoylamino]-1,3,4-hexadecanetriol
  参考文献：
  名称：

  Sugiyama, Shigeo; Honda, Masanori; Komori, Tetsuya, Liebigs Annalen der Chemie, 1990, # 11, p. 1063 - 1068

  摘要：

  DOI：

文献信息

• Sugiyama, Shigeo; Honda, Masanori; Komori, Tetsuya, Liebigs Annalen der Chemie, 1990, # 11, p. 1063 - 1068
  作者：Sugiyama, Shigeo、Honda, Masanori、Komori, Tetsuya

  DOI：——

  日期：——
• SUGIYAMA, SHIGEO;HONDA, MASANORI;KOMORI, TETSUYA, LIEBIGS ANN. CHEM.,(1990) N1, C. 1063-1068
  作者：SUGIYAMA, SHIGEO、HONDA, MASANORI、KOMORI, TETSUYA

  DOI：——

  日期：——
• Sugiyama, Shigeo; Honda, Masanori; Higuchi, Ryuichi, Liebigs Annalen der Chemie, 1991, # 4, p. 349 - 356
  作者：Sugiyama, Shigeo、Honda, Masanori、Higuchi, Ryuichi、Komori, Tetusya

  DOI：——

  日期：——
• Synthesis of a Hematoside Analog Containing Phytosphingosine and α-Hydroxyfatty Acid
  作者：Tetsuji Sugata、Yoko Kan、Yoshiteru Nagaregawa、Tomofumi Miyamoto、Ryuichi Higuchi

  DOI：10.1080/07328309708006548

  日期：1997.8.1

  The hematoside analog 1 [NeuGc alpha(2-->3)Gal beta(1-->4)Glc beta(1-->1)Cer], which contains a phytosphingosine as a sphingoid base and an alpha-hydroxyfatty acid, has been synthesized. Coupling of the methyl (methyl 5-benzyloxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-alpha- and -beta-D-galacto-2-nonulopyranosid)onate 5, prepared from the corresponding 5-acetamido derivative 2, with a lactose derivative 6 afforded sialolactoside 7, which was converted to the corresponding trichloroacetimidate 10. Glycosylation of 10 with the ceramide tribenzoate 12 gave the protected hematoside analog 13, which was deprotected to the hematoside analog 1.