(1R,2'S,4'S,5'R)-2-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-ethane-1,2-diol | 143739-01-9

• 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: (1R,2'S,4'S,5'R)-2-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-ethane-1,2-diol
• 英文别名: (2S,4S,5R)-2-<(2'R)-1'-hydroxy-2'-hydroxyethyl>-4-methyl-5-phenyl-3-p-toluenesulfonyloxazolidine；(2S,4S,5R)-2-<(1'R)-1',2'-dihydroxyethyl>-4-methyl-5-phenyl-3-p-tolylsulfonyloxazolidine；(1R)-1-[(2S,4S,5R)-4-methyl-3-(4-methylphenyl)sulfonyl-5-phenyl-1,3-oxazolidin-2-yl]ethane-1,2-diol
• CAS: 143739-01-9
• 化学式: C₁₉H₂₃NO₅S
• 分子量: 377.461
• InChiKey: HRZGEHPDKKEVNQ-VLQPXKRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1R,2S)-[N-(4-甲基苯基)磺酰基]去甲麻黄碱 在 奎宁环 、 osmium (III) chloride 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 、 苯 为溶剂， 反应 22.5h， 生成 (1R,2'S,4'S,5'R)-2-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-ethane-1,2-diol
  参考文献：
  名称：

  与二苯基膦氧化物的不对称合成：双环缩醛和恶唑烷作为手性助剂

  摘要：

  描述了六个新颖的氧化膦手性助剂的合成。助剂由二苯基膦酰基（Ph 2 PO）基团和脯氨酸衍生的双环氨基缩醛或降麻黄碱衍生的恶唑烷组成。一种助剂用于合成旋光性β-羟基氧化膦。

  DOI：

  10.1016/s0957-4166(96)00451-x

文献信息

• Asymmetric synthesis with diphenylphosphine oxides: Bicyclic aminals and oxazolidines as chiral auxiliaries
  作者：Peter O'Brien、Stuart Warren

  DOI：10.1016/s0957-4166(96)00451-x

  日期：1996.12

  Syntheses of six novel phosphine oxide chiral auxiliaries are described. The auxiliaries are composed of the diphenylphosphinoyl (Ph2PO) group and either proline-derived bicyclic aminals or norephedrine-derived oxazolidines. One auxiliary is used in the synthesis of an optically active β-hydroxy phosphine oxide.

  描述了六个新颖的氧化膦手性助剂的合成。助剂由二苯基膦酰基（Ph 2 PO）基团和脯氨酸衍生的双环氨基缩醛或降麻黄碱衍生的恶唑烷组成。一种助剂用于合成旋光性β-羟基氧化膦。
• Diastereoselective addition of metal-coordinated and ‘naked’ tri-sec-butylborohydrides to a norephedrine-derived 2-acetyloxazolidine
  作者：Leonardo Manzoni、Tullio Pilati、Giovanni Poli、Carlo Scolastico

  DOI：10.1039/c39920001027

  日期：——

  The addition of tri-sec-butylborohydrides to the 2-acetyl-1,3-oxazolidine 1 can be directed with high selectivity to either the Si or the Reπ-carbonyl face under chelating or non-coordinating conditions, respectively.

  在螯合或非配位条件下，将三仲丁基硼氢化物加成到 2-乙酰基-1,3-恶唑烷 1 上，可以分别高选择性地定向到 Si 或 Re-羰基面。
• Eames, Jason; Mitchell, Helen J.; Nelson, Adam, Journal of the Chemical Society. Perkin transactions I, 1999, # 8, p. 1095 - 1104
  作者：Eames, Jason、Mitchell, Helen J.、Nelson, Adam、O'Brien, Peter、Warren, Stuart、Wyatt, Paul

  DOI：——

  日期：——
• Diastereoselective addition of metal-coordinated and “naked” nucleophilic reagents to norephedrine derived 2-acyl-N-tosyl-oxazolidines
  作者：Giovanni Poli、Elisa Maccagni、Leonardo Manzoni、Tullio Pilati、Carlo Scolastico

  DOI：10.1016/s0040-4020(96)01087-3

  日期：1997.2

  The addition of tri-s-butyl borohydrides to the 2-acetyl-1,3-oxazolidine 1 could be directed with high selectivity to either the Si or the Re pi-carbonyl face under chelating or non-coordinating conditions respectively. Addition of hydrides to the corresponding phenyl ketone 2 was highly Si selective only in the former conditions. Grignard reagents and organolithiums add to the methyl ketone 1 with remarkable Si and Re pi-face selectivity respectively. With phenyl ketone 2 only organomagnesium reagents follow the above trend. This data are in accord with a Felkin-type or a stereochemically opposite chelaled mode of addition of these nucleophiles in the absence or in the presence of chelating metal counterions respectively. (C) 1997, Published by Elsevier Science Ltd.