(S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 399559-48-9

• 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: (S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[(1R)-1-hydroxy-3-[(R)-(4-methylphenyl)sulfinyl]but-3-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 399559-48-9
• 化学式: C₂₁H₃₁NO₅S
• 分子量: 409.547
• InChiKey: CPNCBLZNTJFSAW-QLPUUCHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.0h， 生成 tert-butyl (4aS,7RS,8aR,R_S)-2,2-dimethyl-7-[(4-methylphenyl)sulfinyl]hexahydro-5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate
  参考文献：
  名称：

  Diastereoselective Route to Piperidine and Indolizidine Scaffolds From Enantiopure Vinylsulfinyl-Containing Amino Alcohols

  摘要：

  A new route to functionalized piperidine and indolizidine scaffolds, based on the diastereoselective intramolecular Michael cyclization of vinyl-sulfinyl-containing amino alcohols 1-3, has been developed. Pyrolytic elimination of the resulting cycloadducts resulted in the regioselective formation of the corresponding tetrahydropyridines and indolizidines. The observed regiochemical course of this process can be explained mainly in terms of the steric bias imposed by the disposition of the arylsulfinyl group and the concerted syn mechanism accepted for this kind of elimination.

  DOI：

  10.1002/1099-0690(200301)2003:1<217::aid-ejoc217>3.0.co;2-w
• 作为产物：
  描述：

  (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 、 (S_S)-(+)-3-chloro-2-(p-tolylsulfinyl)prop-2-ene 在 氯化铵 sodium iodide 、 zinc(II) chloride 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 、 (S)-4-[(S)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  α-氨基醛与对映体纯的2-亚磺酰基烯丙基的Barbier型非对映选择性烯丙基化。

  摘要：

  使用我们新的手性结构单元（S（s））-3-氯-2-（对甲苯基亚磺酰基）-1-丙烯[（S）在Barbier水溶液的水性Barbier条件下进行非对映选择性烯丙基化的优化程序（s））-1a]以高收率提供对映体纯的亚磺酰基氨基醇，并且据报道有非对映选择性。从与天然α-氨基酸构型相关的α-氨基醛可以实现高水平的非对映异构诱导。

  DOI：

  10.1021/jo016068u

文献信息

• Barbier-Type Diastereoselective Allylation of α-Amino Aldehydes with an Enantiopure 2-Sulfinylallyl Building Block
  作者：Francesc Márquez、Raúl Montoro、Amadeu Llebaria、Elena Lago、Elies Molins、Antonio Delgado

  DOI：10.1021/jo016068u

  日期：2002.1.1

  An optimized procedure for the diastereoselective allylation under aqueous Barbier conditions of a series of alpha-amino aldehydes with our new chiral building block (S(s))-3-chloro-2-(p-tolylsulfinyl)-1-propene [(S(s))-1a] to afford enantiomerically pure sulfinylamino alcohols in good yields and diastereoselectivites is reported. High levels of diastereoinduction can be achieved from alpha-amino aldehydes

  使用我们新的手性结构单元（S（s））-3-氯-2-（对甲苯基亚磺酰基）-1-丙烯[（S）在Barbier水溶液的水性Barbier条件下进行非对映选择性烯丙基化的优化程序（s））-1a]以高收率提供对映体纯的亚磺酰基氨基醇，并且据报道有非对映选择性。从与天然α-氨基酸构型相关的α-氨基醛可以实现高水平的非对映异构诱导。
• Diastereoselective Route to Piperidine and Indolizidine Scaffolds From Enantiopure Vinylsulfinyl-Containing Amino Alcohols
  作者：Raúl Montoro、Francesc Márquez、Amadeu Llebaria、Antonio Delgado

  DOI：10.1002/1099-0690(200301)2003:1<217::aid-ejoc217>3.0.co;2-w

  日期：2003.1

  A new route to functionalized piperidine and indolizidine scaffolds, based on the diastereoselective intramolecular Michael cyclization of vinyl-sulfinyl-containing amino alcohols 1-3, has been developed. Pyrolytic elimination of the resulting cycloadducts resulted in the regioselective formation of the corresponding tetrahydropyridines and indolizidines. The observed regiochemical course of this process can be explained mainly in terms of the steric bias imposed by the disposition of the arylsulfinyl group and the concerted syn mechanism accepted for this kind of elimination.