(1S,2S)-<(Triphenylmethyl)oxy>-(trans-2-nitrocyclopropyl)methane | 148123-98-2

• 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: (1S,2S)-<(Triphenylmethyl)oxy>-(trans-2-nitrocyclopropyl)methane
• CAS: 148123-98-2
• 化学式: C₂₃H₂₁NO₃
• 分子量: 359.425
• InChiKey: VRYSCUUFBNVGBP-GCJKJVERSA-N

物化性质

• 沸点：
  485.6±14.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  (1S,2S)-<(Triphenylmethyl)oxy>-(trans-2-nitrocyclopropyl)methane 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以87%的产率得到(S,S)-(2-Nitrocyclopropyl)methanol
  参考文献：
  名称：

  Synthesis of 3-(trans-2'-Nitrocyclopropyl)alanine, a Constituent of the Natural Peptide-Lactone Hormaomycin

  摘要：

  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.

  DOI：

  10.1021/jo00115a009
• 作为产物：
  描述：

  (2S)-4-Nitro-1-<(triphenylmethyl)oxy>but-2-yl methanesulfonate 在 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以59%的产率得到(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

文献信息

• Final Elucidation of the Absolute Configuration of the Signal Metabolite Hormaomycin
  作者：Boris D. Zlatopolskiy、Karin Loscha、Petra Alvermann、Sergei I. Kozhushkov、Sergej V. Nikolaev、Axel Zeeck、Armin de Meijere

  DOI：10.1002/chem.200400406

  日期：2004.10.4

  The complete absolute configuration of hormaomycin 1 a has been established by HPLC and HPLC/MS experiments with appropriately derivatized 4-propylprolines, (2S,4S)-6 and (2R,4R)-6, as well as 4-(Z)-propenylprolines, cis-5 and trans-5, and also feeding experiments with enantiomerically pure samples of the deuterium-labeled 3-(2'-nitrocyclopropyl)alanine, (2S)-3,3-[D2]15 and (2S)-2,2'-[D2]15, and 4

  荷马霉素1a的完整绝对构型已通过HPLC和HPLC / MS实验确定，其中含有适当衍生的4-丙基脯氨酸（2S，4S）-6和（2R，4R）-6以及4-（Z）-丙烯脯氨酸，顺式5和反式5，以及用氘标记的3-（2'-硝基环丙基）丙氨酸，（2S）-3,3- [D2] 15和（2S）- 2,2'-[D2] 15和4-（Z）-丙烯基脯氨酸2'，4- [D2]-（2S，4R）-5。首次制备了后五个氨基酸，并允许一个人明确地分配了Hormaomycin 1a中最后四个立体中心的迄今未知的绝对构型。另外，还收集了有关该分子生物合成的一些新信息。