(4R,5S)-5-Benzyloxymethyl-4-hydroxymethyl-3-(toluene-4-sulfonyl)-oxazolidin-2-one | 115492-03-0

• 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: (4R,5S)-5-Benzyloxymethyl-4-hydroxymethyl-3-(toluene-4-sulfonyl)-oxazolidin-2-one
• 英文别名: (4R,5S)-4-(hydroxymethyl)-3-(4-methylphenyl)sulfonyl-5-(phenylmethoxymethyl)-1,3-oxazolidin-2-one
• CAS: 115492-03-0
• 化学式: C₁₉H₂₁NO₆S
• 分子量: 391.445
• InChiKey: QRTZVHOHCXDBAB-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 双氧水 、 palladium diacetate 、 lithium trifluoroacetate 作用下， 以 水 、 丙酮 为溶剂， 反应 10.0h， 以75%的产率得到(4R,5S)-5-Benzyloxymethyl-4-hydroxymethyl-3-(toluene-4-sulfonyl)-oxazolidin-2-one
  参考文献：
  名称：

  Pd-Catalyzed Intramolecular Aminohydroxylation of Alkenes with Hydrogen Peroxide as Oxidant and Water as Nucleophile

  摘要：

  A palladium-catalyzed intramolecular aminohydroxylation of alkenes was developed, in which H2O2 was applied as the sole oxidant. A variety of related alkyl alcohols could be successfully obtained with good yields and excellent diastereoselectivities, which directly derived from oxidation cleavage of alkyl C-Pd bond by H2O2. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that major nucleophilic attack of water (S(N)2 type) at high-valent Pd center contributes to the final C-O(H) bond formation.

  DOI：

  10.1021/ja412023b

文献信息

• Cyclofunctionalisation reactions of epoxyalcohol derivatives. 3. cyclisationacyl migration of n-benzoylcarbamates to stereodefined oxazolidinones. A new, diastereospecific route to thiamphenicol.
  作者：S.W. McCombie、T.L. Nagabhushan

  DOI：10.1016/s0040-4039(00)96737-6

  日期：1987.1

  N-Benzoylcarbamates formed from 2,3-epoxyalcohols and PhCONCO undergo clean N to C-2 cyclisation followed by N to O acyl migration on treatment with catalytic sodium imidazolide or other bases. Subsequent benzoate cleavage (NaOMe) is accompanied by equilibration of the N-unsubstituted oxazolidinones; cleavage without significant isomerisation is achieved with MeLi or Zn(BH4)2. This methodology is applied

  由2,3-环氧醇和PhCONCO形成的N-苄基氨基甲酸酯经过干净的N-C-2环化，然后在用催化咪唑钠或其他碱处理时N-O酰基迁移。随后的苯甲酸酯裂解（NaOMe）伴随着N-未取代的恶唑烷酮的平衡; MeLi或Zn（BH4）2可实现无明显异构化的酶切。该方法适用于非对映异构的，6-甲基4-溴苯基砜向外消旋的甲砜霉素的6步转化。
• MCCOMBIE, S. W.;NAGABHUSHAN, T. L., TETRAHEDRON. LETT., 28,(1987) N 45, 5395-5398
  作者：MCCOMBIE, S. W.、NAGABHUSHAN, T. L.

  DOI：——

  日期：——