9H-fluoren-9-ylmethyl (4S)-4-[(1R)-1-acetyloxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate | 946845-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl (4S)-4-[(1R)-1-acetyloxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 946845-45-0
• 化学式: C₂₂H₂₁NO₆
• 分子量: 395.412
• InChiKey: AMFCHHLVGHCHQM-XCLFUZPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl (4S)-4-[(1R)-1-acetyloxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate 在 哌啶 、 盐酸 、 三乙基硅烷 、 4-二甲氨基吡啶 、 aluminum (III) chloride 、 palladium on activated charcoal 、 氢气 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 60.0 ℃ 、100.0 kPa 条件下， 反应 80.17h， 生成 3-[1'-hydroxy-(2'S)-methyl-oct-1'-ylidene]-(5S)-[(1'R)-triisopropylsilyloxy-ethyl]-1-methylpyrrolidine-2,4-dione
  参考文献：
  名称：

  Synthesis, stereochemical assignment, and bioactivity of the Penicillium metabolites penicillenols B1 and B2

  摘要：

  The Penicillium metabolites penicillenols B-1 and B-2 were synthesised for the first time by elimination of a mesylated penicillenol A precursor as obtained from an L-threonine derived tetramic acid. The (Z,S)-and (E,S)-configured diastereomers were identical to the natural compounds as to NMR spectra and optical rotations. Both isomers showed antiproliferative effects against cancer and endothelial cell lines and penicillenol B-1 was also notably antibiotic against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.116
• 作为产物：
  描述：

  O-乙酰基-L-苏氨酸 在 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲苯 为溶剂， 反应 13.0h， 生成 9H-fluoren-9-ylmethyl (4S)-4-[(1R)-1-acetyloxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis, stereochemical assignment, and bioactivity of the Penicillium metabolites penicillenols B1 and B2

  摘要：

  The Penicillium metabolites penicillenols B-1 and B-2 were synthesised for the first time by elimination of a mesylated penicillenol A precursor as obtained from an L-threonine derived tetramic acid. The (Z,S)-and (E,S)-configured diastereomers were identical to the natural compounds as to NMR spectra and optical rotations. Both isomers showed antiproliferative effects against cancer and endothelial cell lines and penicillenol B-1 was also notably antibiotic against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.116

文献信息

• An improved synthesis of Fmoc-N-methyl serine and threonine
  作者：Rajesh H. Bahekar、Pradip A. Jadav、Dipam N. Patel、Vijay M. Prajapati、Arun A. Gupta、Mukul R. Jain、Pankaj R. Patel

  DOI：10.1016/j.tetlet.2007.05.112

  日期：2007.7

  An improved method for the synthesis of Fmoc-N-methyl serine and threonine has been developed, which involves formation and subsequent reduction of the corresponding oxazolidinone with a Lewis acid under mild conditions, with improved yields and shorter reaction times. (C) 2007 Elsevier Ltd. All rights reserved.