(S)-tert-butyl 4-((R)-1-hydroxy-13-methyl-3-oxotetradecyl)-2,2-dimethyloxazolidine-3-carboxylate | 1616618-34-8

• 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: (S)-tert-butyl 4-((R)-1-hydroxy-13-methyl-3-oxotetradecyl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS: 1616618-34-8
• 化学式: C₂₅H₄₇NO₅
• 分子量: 441.652
• InChiKey: OYJOINQCHFKCSM-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  31.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 4-((R)-1-hydroxy-13-methyl-3-oxotetradecyl)-2,2-dimethyloxazolidine-3-carboxylate 在 二乙基甲氧基硼烷 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 4-((4R,6S)-2,2-dimethyl-6-(10-methylundecyl)-1,3-dioxan-4-yl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of the Rosette-Inducing Factor RIF-1 and Analogs

  摘要：

  Studies on the origin of animal multicellularity have increasingly focused on one of the closest living relatives of animals, the choanoflagellate Salpingoeca rosetta. Single cells of S. rosetta can develop into multicellular rosette-shaped colonies through a process of incomplete cytokinesis. Unexpectedly, the initiation of rosette development requires bacterially produced small molecules. Previously, our laboratories reported the planar structure and femtomolar rosette-inducing activity of one rosette-inducing small molecule, dubbed rosette-inducing factor 1 (RIF-1), produced by the Gram-negative Bacteroidetes bacterium Algoriphagus machipongonensis. RIF-1 belongs to the small and poorly explored class of sulfonolipids. Here, we report a modular total synthesis of RIF-1 stereoisomers and structural analogs. Rosette-induction assays using synthetic RIF-1 stereoisomers and naturally occurring analogs defined the absolute stereochemistry of RIF-1 and revealed a remarkably restrictive set of structural requirements for inducing rosette development.

  DOI：

  10.1021/ja5046692
• 作为产物：
  描述：

  (S)-tert-butyl 4-((R,Z)-3-(benzyldimethylsilyl)-1-hydroxy-13-methyltetradec-2-enyl)-2,2-dimethyloxazolidine-3-carboxylate 在 四丁基氟化铵 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.25h， 以82%的产率得到(S)-tert-butyl 4-((R)-1-hydroxy-13-methyl-3-oxotetradecyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of the Rosette-Inducing Factor RIF-1 and Analogs

  摘要：

  Studies on the origin of animal multicellularity have increasingly focused on one of the closest living relatives of animals, the choanoflagellate Salpingoeca rosetta. Single cells of S. rosetta can develop into multicellular rosette-shaped colonies through a process of incomplete cytokinesis. Unexpectedly, the initiation of rosette development requires bacterially produced small molecules. Previously, our laboratories reported the planar structure and femtomolar rosette-inducing activity of one rosette-inducing small molecule, dubbed rosette-inducing factor 1 (RIF-1), produced by the Gram-negative Bacteroidetes bacterium Algoriphagus machipongonensis. RIF-1 belongs to the small and poorly explored class of sulfonolipids. Here, we report a modular total synthesis of RIF-1 stereoisomers and structural analogs. Rosette-induction assays using synthetic RIF-1 stereoisomers and naturally occurring analogs defined the absolute stereochemistry of RIF-1 and revealed a remarkably restrictive set of structural requirements for inducing rosette development.

  DOI：

  10.1021/ja5046692