methyl (2R,3R)-2-amino-3-hydroxy-3-(2-thienyl)propionate | 273223-24-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R,3R)-2-amino-3-hydroxy-3-(2-thienyl)propionate
• 英文别名: Methyl (I+/-R,I(2)R)-I+/--amino-I(2)-hydroxy-2-thiophenepropanoate；methyl (2R,3R)-2-amino-3-hydroxy-3-thiophen-2-ylpropanoate
• CAS: 273223-24-8
• 化学式: C₈H₁₁NO₃S
• 分子量: 201.246
• InChiKey: ZWSAQEJYQISWFP-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R)-2-amino-3-hydroxy-3-(2-thienyl)propionate 在 sodium hydroxide 作用下， 反应 4.0h， 生成 threo-β-thienylserine
  参考文献：
  名称：

  手性甘氨酸烯醇合成子与杂芳醛的立体选择性羟醛加成

  摘要：

  The stereocontrolled addition of (2S)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (1) to heterocyclic aldehydes (2) gives mainly a mixture of syn/anti isomers (3) and (4) whose steric configuration was assigned on the basis of spectroscopic data and accepted model for aldol condensation of 1. The possible conversion of adducts to three beta-substituted heteroaromatic serines is demonstrated.

  DOI：

  10.3987/com-99-s145
• 作为产物：
  描述：

  (1S)-1-[(2'S,5'R)-2',5'-dihydro-2'-isopropyl-3',6'-dimethoxy-5'-pyrazinyl]-1-(2-thienyl)methanol 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以55%的产率得到methyl (2R,3R)-2-amino-3-hydroxy-3-(2-thienyl)propionate
  参考文献：
  名称：

  手性甘氨酸烯醇合成子与杂芳醛的立体选择性羟醛加成

  摘要：

  The stereocontrolled addition of (2S)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (1) to heterocyclic aldehydes (2) gives mainly a mixture of syn/anti isomers (3) and (4) whose steric configuration was assigned on the basis of spectroscopic data and accepted model for aldol condensation of 1. The possible conversion of adducts to three beta-substituted heteroaromatic serines is demonstrated.

  DOI：

  10.3987/com-99-s145

文献信息

• Stereoselective Aldol Addition of a Chiral Glycine Enolate Synthon to Heteroaromatic Aldehydes
  作者：Piero Dalla Croce、Raffaella Ferraccioli、Concetta La Rosa、Enrica Pizzatti

  DOI：10.3987/com-99-s145

  日期：——

  The stereocontrolled addition of (2S)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (1) to heterocyclic aldehydes (2) gives mainly a mixture of syn/anti isomers (3) and (4) whose steric configuration was assigned on the basis of spectroscopic data and accepted model for aldol condensation of 1. The possible conversion of adducts to three beta-substituted heteroaromatic serines is demonstrated.