(2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester | 864924-29-8

• 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: (2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester
• CAS: 864924-29-8
• 化学式: C₁₄H₁₈N₂O₆S
• 分子量: 342.373
• InChiKey: FBGYJAQRKCZGDN-AMIZOPFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  129.77
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Stereochemical Assignment of Intermediates in the Rifamycin Biosynthetic Pathway by Precursor-Directed Biosynthesis

  摘要：

  Natural and semisynthetic rifamycins are clinically important inhibitors of bacterial DNA-dependent RNA polymerase. Although the polyketide-nonribosomal peptide origin of the naphthalene core of rifamycin B is well established, the absolute and relative configuration of both stereocenters introduced by the first polyketide synthase module is obscured by aromatization of the naphthalene ring. To decode the stereochemistry of the rifamycin polyketide precursor, we synthesized all four diastereomers of the biosynthetic substrate for module 2 of the rifamycin synthetase in the form of their N-acetylcysteamine (SNAC) thioester. Only one diastereomer was turned over in vivo into rifamycin B, thus establishing the absolute and relative configuration of the native biosynthetic intermediates.

  DOI：

  10.1021/ja051430y
• 作为产物：
  描述：

  (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 44.0h， 以94%的产率得到(2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester
  参考文献：
  名称：

  Stereochemical Assignment of Intermediates in the Rifamycin Biosynthetic Pathway by Precursor-Directed Biosynthesis

  摘要：

  Natural and semisynthetic rifamycins are clinically important inhibitors of bacterial DNA-dependent RNA polymerase. Although the polyketide-nonribosomal peptide origin of the naphthalene core of rifamycin B is well established, the absolute and relative configuration of both stereocenters introduced by the first polyketide synthase module is obscured by aromatization of the naphthalene ring. To decode the stereochemistry of the rifamycin polyketide precursor, we synthesized all four diastereomers of the biosynthetic substrate for module 2 of the rifamycin synthetase in the form of their N-acetylcysteamine (SNAC) thioester. Only one diastereomer was turned over in vivo into rifamycin B, thus establishing the absolute and relative configuration of the native biosynthetic intermediates.

  DOI：

  10.1021/ja051430y