tert-butyl (4S,1'R,9'S,10'R)-4-(1'-hydroxy-9',10'-methylene-2'-icosynyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 400051-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: tert-butyl (4S,1'R,9'S,10'R)-4-(1'-hydroxy-9',10'-methylene-2'-icosynyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-4-[(1R)-8-[(1S,2R)-2-decylcyclopropyl]-1-hydroxyoct-2-ynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 400051-52-7
• 化学式: C₃₁H₅₅NO₄
• 分子量: 505.782
• InChiKey: UFAAUCONOGNWFC-WXIAYYLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S,1'R,9'S,10'R)-4-(1'-hydroxy-9',10'-methylene-2'-icosynyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 双氧水 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以89%的产率得到tert-butyl (4S,1'R,9'S,10'R)-4-(1'-hydroxy-9',10'-methyleneicosyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  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)-6,7-methylene-1-heptadecanol 在 吡啶 、 正丁基锂 、 sodium iodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (4S,1'R,9'S,10'R)-4-(1'-hydroxy-9',10'-methylene-2'-icosynyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  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