(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid | 864924-27-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid
• CAS: 864924-27-6
• 化学式: C₁₆H₂₅NO₆Si
• 分子量: 355.463
• InChiKey: KMMDVVJDRMQERV-QMTHXVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  109.9
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid 在 palladium on activated charcoal 盐酸 、 氢氟酸 、 氢气 、 N,N'-羰基二咪唑 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 89.5h， 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：

  (R)-4-Benzyl-3-{(2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-2-methyl-propionyl}-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以91%的产率得到(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid
  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