(1'S,1''S,2''S,4R)-4-{1'-hydroxy-2'-[N-(2''-hydroxy-1''-methyl-2''-phenylethyl)-N-methylcarbamoyl]ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 760188-33-8

• 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,1''S,2''S,4R)-4-{1'-hydroxy-2'-[N-(2''-hydroxy-1''-methyl-2''-phenylethyl)-N-methylcarbamoyl]ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS: 760188-33-8
• 化学式: C₂₃H₃₆N₂O₆
• 分子量: 436.549
• InChiKey: PCOBVXPQIGVORW-ZNWBIBPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  99.54
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1'S,1''S,2''S,4R)-4-{1'-hydroxy-2'-[N-(2''-hydroxy-1''-methyl-2''-phenylethyl)-N-methylcarbamoyl]ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 生成 (+)-(1'S,4R)-4-(2'-carboxy-1'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Double Stereodifferentiation in the “Acetate-Type” Aldol Reaction with Garner's Aldehyde. Stereocontrolled Synthesis of Polyhydroxylated γ-Amino Carbonyl Compounds

  摘要：

  The aldol reaction of acetamide enolates with protected chiral alpha-amino-beta-hydroxy aldehyde 1 (Garner's aidehyde) has been performed in a stereocontrolled way under double stereodifferentiation conditions using pseudoephedrine as the additional chiral information source attached to the enolate reagent. In addition, the obtained adduct has been transformed into other valuable chiral building blocks such as gamma-amino-beta,delta-dihydroxy acids, esters, and ketones.

  DOI：

  10.1021/ol0487433
• 作为产物：
  描述：

  外消旋N-乙酰基-伪麻黄碱 、 (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到(1'S,1''S,2''S,4R)-4-{1'-hydroxy-2'-[N-(2''-hydroxy-1''-methyl-2''-phenylethyl)-N-methylcarbamoyl]ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Double Stereodifferentiation in the “Acetate-Type” Aldol Reaction with Garner's Aldehyde. Stereocontrolled Synthesis of Polyhydroxylated γ-Amino Carbonyl Compounds

  摘要：

  The aldol reaction of acetamide enolates with protected chiral alpha-amino-beta-hydroxy aldehyde 1 (Garner's aidehyde) has been performed in a stereocontrolled way under double stereodifferentiation conditions using pseudoephedrine as the additional chiral information source attached to the enolate reagent. In addition, the obtained adduct has been transformed into other valuable chiral building blocks such as gamma-amino-beta,delta-dihydroxy acids, esters, and ketones.

  DOI：

  10.1021/ol0487433