benzyl (3S,5S,6R)-3-(4-azidobutyl)-3-methyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate | 1202003-42-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: benzyl (3S,5S,6R)-3-(4-azidobutyl)-3-methyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 1202003-42-6
• 化学式: C₂₉H₃₀N₄O₄
• 分子量: 498.582
• InChiKey: DWJKOPUFFCGBKO-HFASVGIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (3S,5S,6R)-3-(4-azidobutyl)-3-methyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate 在 氢气 、 palladium dichloride 作用下， 以84%的产率得到(S)-2-methyllysine dihydrochloride
  参考文献：
  名称：

  Enantioselective synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary

  摘要：

  Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (4) was successively alkylated with methyl iodide and 1,4-diiodobutane using a base. In each alkylation step anti-alkylated product formed exclusively. The iodo group was displaced with azide, which served as a precursor for the side-chain amino function. Catalytic hydrogenation with concomitant cleavage of the chiral auxiliary afforded (L)-alpha-Me-Lys-OH (9) in a total of four steps in good yield. (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained from 9 via regioselective benzyloxycarbonylation. Alternately, (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained via Staudinger reduction of azide (8) in a total of six steps in good yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.148
• 作为产物：
  描述：

  benzyl (3S,5S,6R)-3-(4-iodobutyl)-3-methyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate 在 sodium azide 作用下， 以 1,3-二甲基-2-咪唑啉酮 为溶剂， 以91%的产率得到benzyl (3S,5S,6R)-3-(4-azidobutyl)-3-methyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary

  摘要：

  Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (4) was successively alkylated with methyl iodide and 1,4-diiodobutane using a base. In each alkylation step anti-alkylated product formed exclusively. The iodo group was displaced with azide, which served as a precursor for the side-chain amino function. Catalytic hydrogenation with concomitant cleavage of the chiral auxiliary afforded (L)-alpha-Me-Lys-OH (9) in a total of four steps in good yield. (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained from 9 via regioselective benzyloxycarbonylation. Alternately, (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained via Staudinger reduction of azide (8) in a total of six steps in good yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.148

文献信息

• Enantioselective synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary
  作者：Satendra S. Chauhan

  DOI：10.1016/j.tetlet.2009.09.148

  日期：2009.12

  Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (4) was successively alkylated with methyl iodide and 1,4-diiodobutane using a base. In each alkylation step anti-alkylated product formed exclusively. The iodo group was displaced with azide, which served as a precursor for the side-chain amino function. Catalytic hydrogenation with concomitant cleavage of the chiral auxiliary afforded (L)-alpha-Me-Lys-OH (9) in a total of four steps in good yield. (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained from 9 via regioselective benzyloxycarbonylation. Alternately, (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained via Staudinger reduction of azide (8) in a total of six steps in good yield. (C) 2009 Elsevier Ltd. All rights reserved.