(S)-4-benzyloxycarbonylamino-2-oxazolidone | 7705-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-benzyloxycarbonylamino-2-oxazolidone
• 英文别名: ((R)-2-oxo-oxazolidin-4-yl)-carbamic acid benzyl ester；((R)-2-Oxo-oxazolidin-4-yl)-carbamidsaeure-benzylester；4-Benzyloxycarbonylaminooxazolidon-2；Carbamic acid, [(4S)-2-oxo-4-oxazolidinyl]-, phenylmethyl ester；benzyl N-[(4S)-2-oxo-1,3-oxazolidin-4-yl]carbamate
• CAS: 7705-88-6
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: KJFJCCSIVVSPEU-SECBINFHSA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  537.4±40.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyloxycarbonylamino-2-oxazolidone 在 4-二甲氨基吡啶 、 苄基三甲基氢氧化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.67h， 生成 (R)-2-hydroxy-1-tert-butoxycarbonylaminoethylcarbamic acid benzyl ester
  参考文献：
  名称：

  (R)-tert-Butoxycarbonylamino-fluorenylmethoxycarbonyl-glycine from (S)-Benzyloxycarbonyl-serine or from Papain Resolution of the Corresponding Amide or Methyl Ester

  摘要：

  The enantiospecific synthesis of (R)-Boc-(Fmoc)-aminoglycine 7 was achieved. (S)-Cbz-serine 1 was reacted with diphenylphosphoryl azide in the presence of triethylamine to yield cyclic (S) carbamate 2. The ring nitrogen of 2 was protected with a Boc group (3). The cyclic carbamate of 3, was hydrolyzed with benzyltrimethylammonium hydroxide to yield the (R)-enantiomer of alcohol. The oxidation of 4 with pyridinium dichromate yielded the enantiomerically pure (87% ee) (R)Boc-(Cbz)-aminoglycine 5, which was converted to 7 with retention of optical purity. Similarly, starting from (S)-Boc-serine 9, cyclic (S) carbamate 10 was obtained. The ring nitrogen of 10 was protected with a Cbz group (11) with retention of configuration. The cyclic carbamate of 11 was base hydrolyzed to yield 12, the (S)-enantiomer alcohol. Independently Boc-(Fmoc)-aminoglycine amide 13 and BoC-(Fmoc)-aminoglycine methyl ester 14 were resolved using papain. The stereochemistry of the isolated acid was determined to be (R) by coelution an HPLC of its. derivative, : with Marfey's reagent and that of-an authentic sample (7) obtained by enantiospecific synthesis.

  DOI：

  10.1021/jo000736e
• 作为产物：
  描述：

  N-苄氧羰酰基-L-丝氨酸甲酯 在 盐酸 、 乙醇 、 一水合肼 、 溶剂黄146 、 sodium nitrite 作用下， 生成 (S)-4-benzyloxycarbonylamino-2-oxazolidone
  参考文献：
  名称：

  Fruton, Journal of Biological Chemistry, 1942, vol. 146, p. 463,469

  摘要：

  DOI：

文献信息

• Phosphorus in organic synthesis—VII
  作者：K. Ninomiya、T. Shioiri、S. Yamada

  DOI：10.1016/s0040-4020(01)97352-1

  日期：1974.1

  (DPPA). The reaction procedure is quite simple, occurring by refluxing an equimolecular mixture of a carboxylic acid, DPPA, and triethylamine in the presence of a hydroxyl component. Aromatic, aliphatic, and heterocyclic carboxylic acids underwent rearrangements in satisfactory yields. As this modified Curtins reaction is much simpler and less laborious than the classical Curtius reaction and proceeds

  通过叠氮磷酸二苯酯（DPPA）可以将羧酸简单地一步转化为氨基甲酸酯。该反应过程非常简单，通过在羟基组分的存在下使羧酸，DPPA和三乙胺的等分子混合物回流来进行。芳族，脂族和杂环羧酸以令人满意的收率进行了重排。由于这种改良的Curtins反应比经典的Curtius反应简单得多且省力，并且在温和的条件下进行，因此它可能具有广泛的合成用途。
• Fruton, Journal of Biological Chemistry, 1942, vol. 146, p. 463,469
  作者：Fruton

  DOI：——

  日期：——
• (<i>R</i>)-<i>tert</i>-Butoxycarbonylamino-fluorenylmethoxycarbonyl-glycine from (<i>S</i>)-Benzyloxycarbonyl-serine or from Papain Resolution of the Corresponding Amide or Methyl Ester
  作者：Michal Sypniewski、Botond Penke、Lajos Simon、Jean Rivier

  DOI：10.1021/jo000736e

  日期：2000.10.1

  The enantiospecific synthesis of (R)-Boc-(Fmoc)-aminoglycine 7 was achieved. (S)-Cbz-serine 1 was reacted with diphenylphosphoryl azide in the presence of triethylamine to yield cyclic (S) carbamate 2. The ring nitrogen of 2 was protected with a Boc group (3). The cyclic carbamate of 3, was hydrolyzed with benzyltrimethylammonium hydroxide to yield the (R)-enantiomer of alcohol. The oxidation of 4 with pyridinium dichromate yielded the enantiomerically pure (87% ee) (R)Boc-(Cbz)-aminoglycine 5, which was converted to 7 with retention of optical purity. Similarly, starting from (S)-Boc-serine 9, cyclic (S) carbamate 10 was obtained. The ring nitrogen of 10 was protected with a Cbz group (11) with retention of configuration. The cyclic carbamate of 11 was base hydrolyzed to yield 12, the (S)-enantiomer alcohol. Independently Boc-(Fmoc)-aminoglycine amide 13 and BoC-(Fmoc)-aminoglycine methyl ester 14 were resolved using papain. The stereochemistry of the isolated acid was determined to be (R) by coelution an HPLC of its. derivative, : with Marfey's reagent and that of-an authentic sample (7) obtained by enantiospecific synthesis.