2RS,4S,5R-4-Methyl-3-p-methylphenylsulphonyl-2-methoxy-5-phenyl-1,3-oxazolidine | 212912-47-5

• 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: 2RS,4S,5R-4-Methyl-3-p-methylphenylsulphonyl-2-methoxy-5-phenyl-1,3-oxazolidine
• 英文别名: (4S,5R)-2-methoxy-4-methyl-3-(4-methylphenyl)sulfonyl-5-phenyl-1,3-oxazolidine
• CAS: 212912-47-5
• 化学式: C₁₈H₂₁NO₄S
• 分子量: 347.435
• InChiKey: BANGJGCYZLLMNS-LNJPMGEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2RS,4S,5R-4-Methyl-3-p-methylphenylsulphonyl-2-methoxy-5-phenyl-1,3-oxazolidine 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 (1R,2S)-[N-(4-甲基苯基)磺酰基]去甲麻黄碱
  参考文献：
  名称：

  Stereoconvergent crotylstannane addition to nor-ephedrine-derived 2-methoxy oxazolidines. A clue towards a synclinal transition state geometry

  摘要：

  DOI：

  10.1016/s0957-4166(00)86345-4
• 作为产物：
  描述：

  原甲酸三甲酯 、 (1R,2S)-[N-(4-甲基苯基)磺酰基]去甲麻黄碱 在 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 0.5h， 以96%的产率得到2RS,4S,5R-4-Methyl-3-p-methylphenylsulphonyl-2-methoxy-5-phenyl-1,3-oxazolidine
  参考文献：
  名称：

  Bernardi, A.; Piarulli, U.; Poli, G., Bulletin de la Societe Chimique de France, 1990, # 6, p. 751 - 757

  摘要：

  DOI：

文献信息

• Norephedrine derived 2-methoxy oxazolidines as chiral formyl cation equivalents
  作者：Anna Bernardi、Silvia Cardani、Oliviero Carugo、Lino Colombo、Carlo Scolastico、Roberto Villa

  DOI：10.1016/s0040-4039(00)94697-5

  日期：1990.1

  1 followed by a straightforward nondestructive removal of the chiral auxiliary affords the corresponding aldehydes in good e.e. Compound 1 represents the first effective chiral synthetic equivalent of formyl cation.

  路易斯酸与1的甲硅烷基醚催化的反应，然后直接无损地除去手性助剂，从而得到良好的ee中的相应醛。化合物1代表了甲酰基阳离子的第一个有效的手性合成等价物。
• Electrophilic α-formylation of carbonyl compounds using nor-ephedrine-derived 2-metohoxy oxazolidines. A novel asymmetric formation of quaternary stereocenters
  作者：Camillo Palazzi、Giovanni Poli、Carlo Scolastico、Roberto Villa

  DOI：10.1016/s0040-4039(00)97587-7

  日期：1990.1
• A new asymmetric approach toward 5-substituted pyrrolidin-2-one derivatives
  作者：Giovanni Poli、Simone Ciofi Baffoni、Giuliano Giambastiani、Gianna Reginato

  DOI：10.1016/s0040-4020(98)00494-3

  日期：1998.8

  The condensation between a chiral 2-silyloxypyrrole and either achiral or chiral formyl cation equivalents has been studied. The methodology has allowed to build-up 5-substituted pyrrolidin-2-one derivatives with a stereocontrol from good to excellent. The chiral auxiliary located on the silyloxypyrrole showed an intrinsic good level of diastereoface discrimination at C-5. However. the use of a 2-methoxy-3-tosyl-oxazolidine as chiral formylating agent allowed a total stereocontrol in the condensation. A rationale for the observed stereochemical outcome is presented. The stereoselective manipulation of these adducts provided new potentially interesting pyroglutamic aldehyde and prolinal derivatives. whereas treatment with TiCl4 triggered unexpectedly a Pomeranz-Fritsch type intramolecular condensation affording a benzocondensated indolizidinone. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Addition of racemic alkoxyallylstannanes to an enantiomerically pure 2-methoxyoxazolidine: an example of combined mutual diastereoface selection and kinetic resolution
  作者：Anna Bernardi、Giovanni Poli、Carlo Scolastico、Matteo Zanda

  DOI：10.1021/jo00025a001

  日期：1991.12

  The BF3.Et2O-promoted addition of racemic alpha- and gamma-alkoxyallylstannanes 2 or 3 to the 2-methoxyoxazolidine 1 afforded adducts 4 and 5 in diastereomeric ratios up to 95:5 accompanied by enantioenriched gamma-stannanes (R)-3. This behavior is consistent with a fast alpha-to-gamma rearrangement of the alkoxystannanes followed by an enantiomer- as well as mutual diastereoface-discriminating condensation.
• PALAZZI, CAMILLO;POLI, GIOVANNI;SCOLASTICO, CARLO;VILLA, ROBERTO, TETRAHEDRON LETT., 31,(1990) N9, C. 4223-4226
  作者：PALAZZI, CAMILLO、POLI, GIOVANNI、SCOLASTICO, CARLO、VILLA, ROBERTO

  DOI：——

  日期：——