(2S,3R,11R,12S,2'R,5'Z,11'R,12'S)-3,2'-bis(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11',12'-methylene-5'-docosenoylamido)-1-docosanol | 400051-74-3

• 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: (2S,3R,11R,12S,2'R,5'Z,11'R,12'S)-3,2'-bis(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11',12'-methylene-5'-docosenoylamido)-1-docosanol
• 英文别名: (Z,2R)-2-[tert-butyl(dimethyl)silyl]oxy-N-[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-10-[(1R,2S)-2-decylcyclopropyl]-1-hydroxydecan-2-yl]-10-[(1R,2S)-2-decylcyclopropyl]dec-5-enamide
• CAS: 400051-74-3
• 化学式: C₅₈H₁₁₅NO₄Si₂
• 分子量: 946.726
• InChiKey: IEJFXNNRURZOIN-SZGCUKEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.21
• 重原子数：
  65
• 可旋转键数：
  44
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,11R,12S,2'R,5'Z,11'R,12'S)-3,2'-bis(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11',12'-methylene-5'-docosenoylamido)-1-docosanol 在 三氟化硼乙醚 、 四丁基氟化铵 、 sodium methylate 、 氰化汞 、 乙酸肼 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 21.5h， 生成 (2R,5Z)-10-[(1R,2S)-2-decylcyclopropyl]-N-((1S,2R)-9-[(1R,2S)-2-decylcyclopropyl]-2-hydroxy-1-{[2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy]methyl}nonyl)-2-hydroxydec-5-enamide
  参考文献：
  名称：

  Synthesis of a Prenylated and Immunosuppressive Marine Galactosphingolipid with Cyclopropane-Containing Alkyl Chains: (2S,3R,11S,12R,2′′′R,5′′′Z,11′′′S,12′′′R)-Plakoside A and Its (2S,3R,11R,12S,2′′′R,5′′′Z,11′′′R,12′′′S) Isomer

  摘要：

  Plakoside A (1) {(2S,3R,11R*,12S*)-2-[(2'''R,5'''Z,11'''R*, 12'''S*)-2"'-hydroxy-11"',12"'-methylene-5"'-docosenamido] -1-O-[2'-O-(3"-methyl-2"-butenyl)-beta -D-galactopyranosyl]-11,12-methylene-1,3 -docosanediol} is a prenylated galactosphingolipid isolated as an immunosuppressant from the marine sponge Plakortis simplex. (2S,3R,11S,12R,2'''R,5'''Z,11'''S,12'''R)-Plakoside A (1) has been synthesized by combining the sphingosine part 16, the alpha -hydroxy acid part 28, and the prenylated sugar part 33. (2S,3R,11R,12S,2'''R,5'''Z,11'''R, 12'''S)-Plakoside A (1') has also been synthesized.

  DOI：

  10.1002/1099-0690(200110)2001:20<3797::aid-ejoc3797>3.0.co;2-y
• 作为产物：
  描述：

  (2R,5Z)-2-[(tert-butyl)dimethylsilyloxy]-10-[(1R,2S)-2-decylcyclopropyl]dec-5-en-1-ol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 10.0h， 生成 (2S,3R,11R,12S,2'R,5'Z,11'R,12'S)-3,2'-bis(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11',12'-methylene-5'-docosenoylamido)-1-docosanol
  参考文献：
  名称：

  Synthesis of a Prenylated and Immunosuppressive Marine Galactosphingolipid with Cyclopropane-Containing Alkyl Chains: (2S,3R,11S,12R,2′′′R,5′′′Z,11′′′S,12′′′R)-Plakoside A and Its (2S,3R,11R,12S,2′′′R,5′′′Z,11′′′R,12′′′S) Isomer

  摘要：

  Plakoside A (1) {(2S,3R,11R*,12S*)-2-[(2'''R,5'''Z,11'''R*, 12'''S*)-2"'-hydroxy-11"',12"'-methylene-5"'-docosenamido] -1-O-[2'-O-(3"-methyl-2"-butenyl)-beta -D-galactopyranosyl]-11,12-methylene-1,3 -docosanediol} is a prenylated galactosphingolipid isolated as an immunosuppressant from the marine sponge Plakortis simplex. (2S,3R,11S,12R,2'''R,5'''Z,11'''S,12'''R)-Plakoside A (1) has been synthesized by combining the sphingosine part 16, the alpha -hydroxy acid part 28, and the prenylated sugar part 33. (2S,3R,11R,12S,2'''R,5'''Z,11'''R, 12'''S)-Plakoside A (1') has also been synthesized.

  DOI：

  10.1002/1099-0690(200110)2001:20<3797::aid-ejoc3797>3.0.co;2-y

文献信息

• Synthesis of a Prenylated and Immunosuppressive Marine Galactosphingolipid with Cyclopropane-Containing Alkyl Chains: (2S,3R,11S,12R,2′′′R,5′′′Z,11′′′S,12′′′R)-Plakoside A and Its (2S,3R,11R,12S,2′′′R,5′′′Z,11′′′R,12′′′S) Isomer
  作者：Masanori Seki、Kenji Mori

  DOI：10.1002/1099-0690(200110)2001:20<3797::aid-ejoc3797>3.0.co;2-y

  日期：2001.10

  Plakoside A (1) (2S,3R,11R*,12S*)-2-[(2'''R,5'''Z,11'''R*, 12'''S*)-2"'-hydroxy-11"',12"'-methylene-5"'-docosenamido] -1-O-[2'-O-(3"-methyl-2"-butenyl)-beta -D-galactopyranosyl]-11,12-methylene-1,3 -docosanediol} is a prenylated galactosphingolipid isolated as an immunosuppressant from the marine sponge Plakortis simplex. (2S,3R,11S,12R,2'''R,5'''Z,11'''S,12'''R)-Plakoside A (1) has been synthesized by combining the sphingosine part 16, the alpha -hydroxy acid part 28, and the prenylated sugar part 33. (2S,3R,11R,12S,2'''R,5'''Z,11'''R, 12'''S)-Plakoside A (1') has also been synthesized.