(2S,3R,11R,12S,2'R,5'Z,11'R,12'S)-1,3,2'-tris(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11',12'-methylene-5'-docosenoylamido)docosane | 400051-73-2

• 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)-1,3,2'-tris(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11',12'-methylene-5'-docosenoylamido)docosane
• 英文别名: (Z,2R)-N-[(2S,3R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-10-[(1R,2S)-2-decylcyclopropyl]decan-2-yl]-2-[tert-butyl(dimethyl)silyl]oxy-10-[(1R,2S)-2-decylcyclopropyl]dec-5-enamide
• CAS: 400051-73-2
• 化学式: C₆₄H₁₂₉NO₄Si₃
• 分子量: 1060.99
• InChiKey: XVJPEUGBTBINFP-IGEVNNMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.24
• 重原子数：
  72
• 可旋转键数：
  47
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 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)-1,3,2'-tris(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11',12'-methylene-5'-docosenoylamido)docosane 在 10percent aq. TFA 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以35%的产率得到(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
• 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 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 7.0h， 生成 (2S,3R,11R,12S,2'R,5'Z,11'R,12'S)-1,3,2'-tris(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

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.