(2S,3R,11R,12S,2'''R,5'''Z,11'''R,12'''S)-1-O-[3',4',6'-tri-O-acetyl-2'-O-(2''-chloroacetyl)-β-D-galactopyranosyl]-3,2'''-bis(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11''',12'''-methylene-5'''-docosenoylamido)docosane | 400051-75-4

• 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)-1-O-[3',4',6'-tri-O-acetyl-2'-O-(2''-chloroacetyl)-β-D-galactopyranosyl]-3,2'''-bis(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11''',12'''-methylene-5'''-docosenoylamido)docosane
• CAS: 400051-75-4
• 化学式: C₇₂H₁₃₂ClNO₁₃Si₂
• 分子量: 1311.46
• InChiKey: WUAWOMKCGIELND-DTPDFZQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.53
• 重原子数：
  89.0
• 可旋转键数：
  50.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  171.22
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,11R,12S,2'''R,5'''Z,11'''R,12'''S)-1-O-[3',4',6'-tri-O-acetyl-2'-O-(2''-chloroacetyl)-β-D-galactopyranosyl]-3,2'''-bis(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11''',12'''-methylene-5'''-docosenoylamido)docosane 在 乙酸肼 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 6.0h， 以74%的产率得到(2S,3R,11R,12S,2'''R,5'''Z,11'''R,12'''S)-1-O-[3',4',6'-tri-O-acetyl-β-D-galactopyranosyl]-3,2'''-bis(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11''',12'''-methylene-5'''-docosenoylamido)docosane
  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 、 氰化汞 、 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 、 硝基甲烷 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 12.0h， 生成 (2S,3R,11R,12S,2'''R,5'''Z,11'''R,12'''S)-1-O-[3',4',6'-tri-O-acetyl-2'-O-(2''-chloroacetyl)-β-D-galactopyranosyl]-3,2'''-bis(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11''',12'''-methylene-5'''-docosenoylamido)docosane
  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