(S)-3-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-2-oxazolidone | 306773-85-3

• 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)-3-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-2-oxazolidone
• 英文别名: (R)-Benzyl 4-((tert-butoxycarbonyl)amino)-2-oxooxazolidine-3-carboxylate；benzyl (4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 306773-85-3
• 化学式: C₁₆H₂₀N₂O₆
• 分子量: 336.345
• InChiKey: NWVQQBLTHUTMMB-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-2-oxazolidone 在 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 0.75h， 以68%的产率得到(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：

  氯甲酸苄酯 、 2-oxooxazolidin-4-ylcarbamic acid tert-butyl ester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到(S)-3-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-2-oxazolidone
  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

文献信息

• (<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.