(2R,3S,4S)-4-chloro-2-methyl-3-phenyl-4-((R)-p-tolylsulfinyl)butyric acid tert-butyl ester | 1022912-14-6

• 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: (2R,3S,4S)-4-chloro-2-methyl-3-phenyl-4-((R)-p-tolylsulfinyl)butyric acid tert-butyl ester
• 英文别名: tert-butyl (2R,3S,4S)-4-chloro-2-methyl-4-[(R)-(4-methylphenyl)sulfinyl]-3-phenylbutanoate
• CAS: 1022912-14-6
• 化学式: C₂₂H₂₇ClO₃S
• 分子量: 406.974
• InChiKey: BWFVOSPLOMIOCR-MTADFXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-4-chloro-2-methyl-3-phenyl-4-((R)-p-tolylsulfinyl)butyric acid tert-butyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides

  摘要：

  Treatment of optically active 1-chlorovinyl p-tolyl sulfoxides with two different substituents at the 2-position, which were synthesized from aldehydes or unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in two or three steps, with the lithium enolate of carboxylic acid tert-butyl esters gave the adducts with substituents at the alpha- and beta-position with high 1,3- and 1,4-chiral induction from the stereogenic sulfur center in high yields. The adducts were converted to optically active esters and gamma-lactones having stereogenic centers at the alpha- and beta-position in good to high yields. This procedure offers a new method for a synthesis of optically active carboxylic acid derivatives with stereogenic centers at the alpha- and beta-position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.040
• 作为产物：
  描述：

  1-[(R)-[(Z)-1-chloro-2-phenylethenyl]sulfinyl]-4-methylbenzene 、 丙酸叔丁酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到(2R,3S,4S)-4-chloro-2-methyl-3-phenyl-4-((R)-p-tolylsulfinyl)butyric acid tert-butyl ester
  参考文献：
  名称：

  An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides

  摘要：

  Treatment of optically active 1-chlorovinyl p-tolyl sulfoxides with two different substituents at the 2-position, which were synthesized from aldehydes or unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in two or three steps, with the lithium enolate of carboxylic acid tert-butyl esters gave the adducts with substituents at the alpha- and beta-position with high 1,3- and 1,4-chiral induction from the stereogenic sulfur center in high yields. The adducts were converted to optically active esters and gamma-lactones having stereogenic centers at the alpha- and beta-position in good to high yields. This procedure offers a new method for a synthesis of optically active carboxylic acid derivatives with stereogenic centers at the alpha- and beta-position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.040

文献信息

• An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides
  作者：Shimpei Sugiyama、Nobuhito Nakaya、Tsuyoshi Satoh

  DOI：10.1016/j.tetasy.2008.01.040

  日期：2008.3

  Treatment of optically active 1-chlorovinyl p-tolyl sulfoxides with two different substituents at the 2-position, which were synthesized from aldehydes or unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in two or three steps, with the lithium enolate of carboxylic acid tert-butyl esters gave the adducts with substituents at the alpha- and beta-position with high 1,3- and 1,4-chiral induction from the stereogenic sulfur center in high yields. The adducts were converted to optically active esters and gamma-lactones having stereogenic centers at the alpha- and beta-position in good to high yields. This procedure offers a new method for a synthesis of optically active carboxylic acid derivatives with stereogenic centers at the alpha- and beta-position. (C) 2008 Elsevier Ltd. All rights reserved.