(2S,3S,4R)-2-docosanoylamino-1,3,4-octadecanetriol | 164576-03-8

• 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-docosanoylamino-1,3,4-octadecanetriol
• 英文别名: N-(docosanoyl)-4R-hydroxysphinganine；N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]docosanamide
• CAS: 164576-03-8
• 化学式: C₄₀H₈₁NO₄
• 分子量: 640.087
• InChiKey: CIMNZQFRNXDRER-HIERITDVSA-N

物化性质

• 沸点：
  757.2±60.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.5
• 重原子数：
  45
• 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：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-docosanoylamino-1,3,4-octadecanetriol 在 吡啶 、 重铬酸吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (2S,3S)-2-docosanoylamino-1,3-octadecanediol-4-one
  参考文献：
  名称：

  Sphingosine and phytosphingosine from D-threose synthesis of a 4-keto-ceramide

  摘要：

  Reaction of 2,4-O-benzylidene-D-threose 3 with tetradecyl magnesium bromide furnished D-arabino- and L-xylo-octadecane-1,2,3,4-tetrols 5a,x. Regioselective oxidation of the 4-OH group gave 4-keto-D-erythro-derivative 6 which can be reduced with acetaldehyde in a SmI2-catalyzed Tishtshenko reaction to afford exclusively 5a. Regioselective 2-O-mesylation of 5a (--> 7a) and then acid catalyzed debenzylation afforded exclusively 2-O-mesyl-tetrol 9a. Reaction with NaN3 and ensuing azide reduction furnished D-ribo-C-18-phytosphingosine (2) in high overall yield. Treatment of 2-O-mesyl derivatives 7a,x with NaN3 and then with 4-nitrobenzenesulfonyl chloride in pyridine afforded 11r,l. Elimination with DBU or, alternatively, by treatment with phenylselenide and then with H2O2, gave known 1,3-O-benzylidene protected azidosphingosine 14, which can be readily converted into sphingosine (1). Transformation of 2 into ceramide 15, selective 1,3-O-silyl protection, oxidation of the 4-OH group (--> 17) and then desilylation afforded the 4-keto ceramide 18 found in a marine sponge. Reduction of 17 offers a convenient possibility for radioactive labelling of ceramides with tritium.

  DOI：

  10.1016/s0957-4166(00)86295-3
• 作为产物：
  描述：

  (2R,3S)-1,3-O-benzylidene-1,2,3-octadecanetriol-4-one 在 吡啶 、 sodium azide 、 samarium diiodide 、 三氟化硼乙醚 、 硫化氢 、 水 、 sodium methylate 、 sodium acetate 、 乙醛 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 (2S,3S,4R)-2-docosanoylamino-1,3,4-octadecanetriol
  参考文献：
  名称：

  Sphingosine and phytosphingosine from D-threose synthesis of a 4-keto-ceramide

  摘要：

  Reaction of 2,4-O-benzylidene-D-threose 3 with tetradecyl magnesium bromide furnished D-arabino- and L-xylo-octadecane-1,2,3,4-tetrols 5a,x. Regioselective oxidation of the 4-OH group gave 4-keto-D-erythro-derivative 6 which can be reduced with acetaldehyde in a SmI2-catalyzed Tishtshenko reaction to afford exclusively 5a. Regioselective 2-O-mesylation of 5a (--> 7a) and then acid catalyzed debenzylation afforded exclusively 2-O-mesyl-tetrol 9a. Reaction with NaN3 and ensuing azide reduction furnished D-ribo-C-18-phytosphingosine (2) in high overall yield. Treatment of 2-O-mesyl derivatives 7a,x with NaN3 and then with 4-nitrobenzenesulfonyl chloride in pyridine afforded 11r,l. Elimination with DBU or, alternatively, by treatment with phenylselenide and then with H2O2, gave known 1,3-O-benzylidene protected azidosphingosine 14, which can be readily converted into sphingosine (1). Transformation of 2 into ceramide 15, selective 1,3-O-silyl protection, oxidation of the 4-OH group (--> 17) and then desilylation afforded the 4-keto ceramide 18 found in a marine sponge. Reduction of 17 offers a convenient possibility for radioactive labelling of ceramides with tritium.

  DOI：

  10.1016/s0957-4166(00)86295-3

文献信息

• Substrate specificity, kinetic properties and inhibition by fumonisin B1 of ceramide synthase isoforms from Arabidopsis
  作者：Kyle D. Luttgeharm、Edgar B. Cahoon、Jonathan E. Markham

  DOI：10.1042/bj20150824

  日期：2016.3.1

  Ceramides are organizing components of sphingolipids in the eukaryotic cell. Three ceramide synthase isoforms are found in Arabidopsis thaliana each with specific substrate preferences and sensitivity to inhibitors and activators.

  神经酰胺是真核细胞中鞘磷脂的组织成分。拟南芥中有三种神经酰胺合成酶异构体，每种异构体都有特定的底物偏好以及对抑制剂和激活剂的敏感性。
• Wild, Robert; Schmidt, Richard R., Liebigs Annalen, 1995, # 5, p. 755 - 764
  作者：Wild, Robert、Schmidt, Richard R.

  DOI：——

  日期：——
• Synthesis of ganglioside M5 from sea urchin egg
  作者：Toshihiro Yamamoto、Tadashi Teshima、Umihito Saitoh、Motonori Hoshi、Tetsuo Shiba

  DOI：10.1016/s0040-4039(00)77010-9

  日期：1994.4

  A main component of ganglioside M5 from egg of the sea urchin, Anthocidaris crassispina, Neu5Gc alpha 2-->6Glc beta 1-->1Cer (1), which has N-glycolyl group in neuraminic acid part, as well as phytosphingosine and saturated nonhydroxy fatty acid in ceramide part was first synthesized starting from N-acetylneuraminic acid.
• METHOD FOR PRODUCING N-ACYLAMINO TRIOL DERIVATIVES
  申请人：Kao Corporation

  公开号：EP2757090B1

  公开（公告）日：2017-04-26
• Sphingosine and phytosphingosine from D-threose synthesis of a 4-keto-ceramide
  作者：Robert Wild、Richard R. Schmidt

  DOI：10.1016/s0957-4166(00)86295-3

  日期：1994.11

  Reaction of 2,4-O-benzylidene-D-threose 3 with tetradecyl magnesium bromide furnished D-arabino- and L-xylo-octadecane-1,2,3,4-tetrols 5a,x. Regioselective oxidation of the 4-OH group gave 4-keto-D-erythro-derivative 6 which can be reduced with acetaldehyde in a SmI2-catalyzed Tishtshenko reaction to afford exclusively 5a. Regioselective 2-O-mesylation of 5a (--> 7a) and then acid catalyzed debenzylation afforded exclusively 2-O-mesyl-tetrol 9a. Reaction with NaN3 and ensuing azide reduction furnished D-ribo-C-18-phytosphingosine (2) in high overall yield. Treatment of 2-O-mesyl derivatives 7a,x with NaN3 and then with 4-nitrobenzenesulfonyl chloride in pyridine afforded 11r,l. Elimination with DBU or, alternatively, by treatment with phenylselenide and then with H2O2, gave known 1,3-O-benzylidene protected azidosphingosine 14, which can be readily converted into sphingosine (1). Transformation of 2 into ceramide 15, selective 1,3-O-silyl protection, oxidation of the 4-OH group (--> 17) and then desilylation afforded the 4-keto ceramide 18 found in a marine sponge. Reduction of 17 offers a convenient possibility for radioactive labelling of ceramides with tritium.