(2S)-4-Nitro-1-<(triphenylmethyl)oxy>butan-2-ol | 148123-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2S)-4-Nitro-1-<(triphenylmethyl)oxy>butan-2-ol
• CAS: 148123-94-8
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: XPWQWZNAJDBNPQ-QFIPXVFZSA-N

反应信息

• 作为反应物：
  描述：

  (2S)-4-Nitro-1-<(triphenylmethyl)oxy>butan-2-ol 在 sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.25h， 生成 (1S,2S)-<(Triphenylmethyl)oxy>-(trans-2-nitrocyclopropyl)methane
  参考文献：
  名称：

  Synthesis of 3-(trans-2′-nitrocyclopropyl)alanine: An unusual natural amino acid

  摘要：

  Racemic (trans-2'-nitrocyclopropyl)methanol rac-7 is prepared in three steps from t-butyl acrylate, while enantiopure (1'S,2'S)-7 and (1'R,2'R)-7 is obtained in six steps from (R)- and (S)-2,3-O-isopropylideneglyceraldehyde, respectively. The alcohol 7 can be transformed to the bromide 8 and this in turn coupled with the glycine equivalent 2-(diphenylmethylenamino)acetate 9 to yield 3-(trans-2'-nitrocyclopropyl)alanine (Ala(3-Ncp)) 11, after deprotection. The natural material, part of the peptide-lactone hormaomycin, has (1'R,2'R)-configuration, as determined by comparison with the synthesized authentic compounds.

  DOI：

  10.1016/s0040-4039(00)91962-2
• 作为产物：
  描述：

  三苯基氯甲烷 、 (S)-4-nitrobutane-1,2-diol 在 吡啶 作用下， 反应 48.0h， 以87%的产率得到(2S)-4-Nitro-1-<(triphenylmethyl)oxy>butan-2-ol
  参考文献：
  名称：

  Synthesis of 3-(trans-2′-nitrocyclopropyl)alanine: An unusual natural amino acid

  摘要：

  Racemic (trans-2'-nitrocyclopropyl)methanol rac-7 is prepared in three steps from t-butyl acrylate, while enantiopure (1'S,2'S)-7 and (1'R,2'R)-7 is obtained in six steps from (R)- and (S)-2,3-O-isopropylideneglyceraldehyde, respectively. The alcohol 7 can be transformed to the bromide 8 and this in turn coupled with the glycine equivalent 2-(diphenylmethylenamino)acetate 9 to yield 3-(trans-2'-nitrocyclopropyl)alanine (Ala(3-Ncp)) 11, after deprotection. The natural material, part of the peptide-lactone hormaomycin, has (1'R,2'R)-configuration, as determined by comparison with the synthesized authentic compounds.

  DOI：

  10.1016/s0040-4039(00)91962-2

文献信息

• Synthesis of 3-(trans-2'-Nitrocyclopropyl)alanine, a Constituent of the Natural Peptide-Lactone Hormaomycin
  作者：Juergen Zindel、Armin de Meijere

  DOI：10.1021/jo00115a009

  日期：1995.5

  The peptide-lactone hormaomycin 1a produced by Streptomyces griseoflavus contains two molecules of 3-(trans-2'-nitrocyclopropyl)alanine [Ala(3-Ncp)] (6). In order to determine the unknown absolute configurations of these unusual natural amino acid molecules, which supposedly are essential for the biological activity of 1a, enantiopure alcohols (trans-2-nitrocyclopropyl)methanol [(1S,2S)-13 and (1R,2R)-13] have been prepared in six steps from (R)- and (S)-2,3-O-isopropylideneglyceral-dehyde (17). The alcohols 13 were transformed to the bromides 23, and these in turn were coupled with suitable glycine equivalents like 2-[(diphenylmethylene)amino]acetates (24) to yield (2R/S,1'S,2'S)- and (2R/S,1'R,2'R)-3-(trans-2'-nitrocyclopropyl)alanines (6), after deprotection. The natural compound la contains one molecule each with (2R,1'R,2'R)- and (2S,1'R,2'R)-configuration, as established by comparison of the hydrolysate from natural la with the synthesized samples of (2R/S,1'R,2'R)-6 and (2R/S,1'S,2'S)-6.