(1'S,2''S,4''S,5''R)-toluene-4-sulfonic acid 2'-hydroxy-2'-[4''-methyl-5''-phenyl-3''-(toluene-4'''-sulfonyl)-oxazolidin-2''-yl]-propyl ester | 166189-46-4

• 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: (1'S,2''S,4''S,5''R)-toluene-4-sulfonic acid 2'-hydroxy-2'-[4''-methyl-5''-phenyl-3''-(toluene-4'''-sulfonyl)-oxazolidin-2''-yl]-propyl ester
• CAS: 166189-46-4
• 化学式: C₂₇H₃₁NO₇S₂
• 分子量: 545.678
• InChiKey: LUCLJYQYJQTJTJ-ZYEMSUIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110.21
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1'S,2''S,4''S,5''R)-toluene-4-sulfonic acid 2'-hydroxy-2'-[4''-methyl-5''-phenyl-3''-(toluene-4'''-sulfonyl)-oxazolidin-2''-yl]-propyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以77%的产率得到(2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine
  参考文献：
  名称：

  Diastereoselective addition of metal-coordinated and “naked” nucleophilic reagents to norephedrine derived 2-acyl-N-tosyl-oxazolidines

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(96)01087-3
• 作为产物：
  描述：

  (2S,4S,5R)-2-isopropenyl-4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidine 在 4-二甲氨基吡啶 、 osmium (III) chloride 、 十二/十四烷基二甲基氧化胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 (1'S,2''S,4''S,5''R)-toluene-4-sulfonic acid 2'-hydroxy-2'-[4''-methyl-5''-phenyl-3''-(toluene-4'''-sulfonyl)-oxazolidin-2''-yl]-propyl ester
  参考文献：
  名称：

  Diastereoselective addition of metal-coordinated and “naked” nucleophilic reagents to norephedrine derived 2-acyl-N-tosyl-oxazolidines

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(96)01087-3