(4R,3'Z,9'S,10'R)-4-(9',10'-methylene-3'-icosenyl)-2,2-dimethyl-1,3-dioxolane | 339195-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,3'Z,9'S,10'R)-4-(9',10'-methylene-3'-icosenyl)-2,2-dimethyl-1,3-dioxolane
• 英文别名: (4R)-4-[(Z)-8-[(1S,2R)-2-decylcyclopropyl]oct-3-enyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 339195-18-5
• 化学式: C₂₆H₄₈O₂
• 分子量: 392.666
• InChiKey: NNQRJDZJBYOBGO-DSPXDCNLSA-N

物化性质

• 沸点：
  462.0±20.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,3'Z,9'S,10'R)-4-(9',10'-methylene-3'-icosenyl)-2,2-dimethyl-1,3-dioxolane 在 咪唑 、 盐酸 、 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 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 34.0h， 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 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：

  (6S,7R)-1-bromo-6,7-methyleneheptadecane 在 sodium hexamethyldisilazane 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 60.17h， 生成 (4R,3'Z,9'S,10'R)-4-(9',10'-methylene-3'-icosenyl)-2,2-dimethyl-1,3-dioxolane
  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 (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.