(2S,3R,11S,12R,2'R,5'Z,11'S,12'R)-1,3,2'-tris(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11',12'-methylene-5'-docosenoylamido)docosane | 339195-24-3

• 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,11S,12R,2'R,5'Z,11'S,12'R)-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-[(1S,2R)-2-decylcyclopropyl]decan-2-yl]-2-[tert-butyl(dimethyl)silyl]oxy-10-[(1S,2R)-2-decylcyclopropyl]dec-5-enamide
• CAS: 339195-24-3
• 化学式: C₆₄H₁₂₉NO₄Si₃
• 分子量: 1060.99
• InChiKey: XVJPEUGBTBINFP-SQAWWCQLSA-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,11S,12R,2'R,5'Z,11'S,12'R)-1,3,2'-tris(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11',12'-methylene-5'-docosenoylamido)docosane 在 三氟化硼乙醚 、 四丁基氟化铵 、 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 24.0h， 生成 [(2R,3S,4S,5R,6R)-3,4-diacetyloxy-6-[(2S,3R)-10-[(1S,2R)-2-decylcyclopropyl]-2-[[(Z,2R)-10-[(1S,2R)-2-decylcyclopropyl]-2-hydroxydec-5-enoyl]amino]-3-hydroxydecoxy]-5-(3-methylbut-2-enoxy)oxan-2-yl]methyl acetate
  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：

  (1S,2R)-2-(hydroxymethyl)cyclopropane-1-methyl acetate 在 吡啶 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 正丁基锂 、 2-甲基-2-丁烯 、 草酰氯 、 dilithium tetrachlorocuprate 、 四溴化碳 、 四丁基氟化铵 、 双氧水 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 三氟乙酸 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (2S,3R,11S,12R,2'R,5'Z,11'S,12'R)-1,3,2'-tris(tert-butyldimethylsilyloxy)-11,12-methylene-2-(11',12'-methylene-5'-docosenoylamido)docosane
  参考文献：
  名称：

  Synthesis of (2 S ,3 R ,11 S ,12 R ,2‴ R ,11‴ S ,12‴ R )-plakoside A, a prenylated and immunosuppressive marine galactosphingolipid with cyclopropane-containing alkyl chains

  摘要：

  Plakoside A (1) is a prenylated galactosphingolipid isolated from the marine sponge Plakoartis simplex and is strongly immunosuppressive without cytotoxicity. (2S,3R,11S,12R,2"'R,11"'S, 12'''R)-plakoside A (1) was synthesized by combining sphingosine part 16, alpha -hydroxy acid part 24 and prenylated sugar part 29. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00175-7

文献信息

• Synthesis of (2 S ,3 R ,11 S ,12 R ,2‴ R ,11‴ S ,12‴ R )-plakoside A, a prenylated and immunosuppressive marine galactosphingolipid with cyclopropane-containing alkyl chains
  作者：Masanori Seki、Akihiro Kayo、Kenji Mori

  DOI：10.1016/s0040-4039(01)00175-7

  日期：2001.3

  Plakoside A (1) is a prenylated galactosphingolipid isolated from the marine sponge Plakoartis simplex and is strongly immunosuppressive without cytotoxicity. (2S,3R,11S,12R,2"'R,11"'S, 12'''R)-plakoside A (1) was synthesized by combining sphingosine part 16, alpha -hydroxy acid part 24 and prenylated sugar part 29. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.