2-oxooxazolidin-4-ylcarbamic acid tert-butyl ester | 82933-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-oxooxazolidin-4-ylcarbamic acid tert-butyl ester
• 英文别名: (S)-4-tert-butoxycarbonylamino-2-oxazolidone；tert-Butyl [(4S)-2-oxo-1,3-oxazolidin-4-yl]carbamate；tert-butyl N-[(4S)-2-oxo-1,3-oxazolidin-4-yl]carbamate
• CAS: 82933-44-6
• 化学式: C₈H₁₄N₂O₄
• 分子量: 202.21
• InChiKey: WVWCVWDDPVIESA-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2-oxooxazolidin-4-ylcarbamic acid tert-butyl ester 在 苄基三甲基氢氧化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 0.75h， 生成 (S)-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：

  BOC-L-丝氨酸 在 polymer-supported diphenylphosphoryl azide 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以60%的产率得到2-oxooxazolidin-4-ylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  Lu, Yuhua; Taylor, Richard T., Heterocycles, 2004, vol. 62, p. 869 - 876

  摘要：

  DOI：

文献信息

• O-Sulfated .beta.-lactam hydroxamic acids (monosulfactams). Novel monocyclic .beta.-lactam antibiotics of synthetic origin
  作者：E. M. Gordon、M. A. Ondetti、Jelka Pluscec、C. M. Cimarusti、D. P. Bonner、R. B. Sykes

  DOI：10.1021/ja00386a035

  日期：1982.11
• Lu, Yuhua; Taylor, Richard T., Heterocycles, 2004, vol. 62, p. 869 - 876
  作者：Lu, Yuhua、Taylor, Richard T.

  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.