1β-(4-hydroxyphenyl)-1-deoxy-D-ribofuranose | 212392-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1β-(4-hydroxyphenyl)-1-deoxy-D-ribofuranose
• 英文别名: 4-(β-D-ribofuranosyl)hydroxybenzene；4-(beta-d-Ribofuranosyl)hydroxybenzene；(2R,3S,4R,5S)-2-(hydroxymethyl)-5-(4-hydroxyphenyl)oxolane-3,4-diol
• CAS: 212392-46-6
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: VFCZYCLQBCNWEC-DBIOUOCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1β-(4-hydroxyphenyl)-1-deoxy-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以77%的产率得到1β-(4-hydroxyphenyl)-1-deoxy-D-ribofuranose
  参考文献：
  名称：

  钯催化卤代芳基C-核苷的羟基化反应合成苯酚和吡啶酮C-核糖核苷和2'-脱氧核糖核苷

  摘要：

  核糖和脱氧核糖系列中的苯酚和吡啶酮C-核苷是由钯催化的羟基化反应，由相应的TBS保护的溴苯基和溴或氯吡啶基C-核苷在温和条件下使用Buchwald型配体制备的。在某些情况下，观察到5'-OH的部分或完全甲硅烷基化。游离核苷（7个实施例）在由TBS保护基团用Et切割好的总产率得到3 N˙3HF。 C-核苷-钯催化-羟基化-苯酚-吡啶酮

  DOI：

  10.1055/s-0030-1258318

文献信息

• The Conversion of a Phenol to an Aniline Occurs in the Biochemical Formation of the 1-(4-Aminophenyl)-1-deoxy-<scp>d</scp>-ribitol Moiety in Methanopterin
  作者：Robert H. White

  DOI：10.1021/bi200362w

  日期：2011.7.12

  Recent work has demonstrated that 4-hydroxybenzoic acid is the in vivo precursor to the 1-(4-aminophenyl)-1-deoxy-D-ribitol (APDR) moiety present in the C-1 carrier coenzyme methanopterin present in the methanogenic archaea. For this transformation to occur, the hydroxyl group of the 4-hydroxybenzoic acid must be replaced with an amino group at some point in the biosynthetic pathway. Using stable isotopically labeled precursors and liquid chromatography with electrospray-ionization mass spectroscopy, the first step of this transformation in Methanocaldococcus jannaschii occurs by the reaction of 4-hydroxybenzoic acid with phosphoribosyl pyrophosphate (PRPP) to form 4-(beta-D-ribofuranosyl)hydroxybenzene 5'-phosphate (beta-RAH-P). The beta-RAH-P then condenses with L-aspartate in the presence of ATP to form 4-(beta-D-ribofuranosyl)-N-succinylaminobenzene 5'-phosphate (beta-RFSA-P). Elimination of fumarate from beta-RFSA-P produces 4-(beta-D-ribofuranosyl)aminobenzene S'-phosphate (beta-RFA-P), the known precursor to the APDR moiety of methanopterin [White, R. H. (1996) Biochemistry 35, 3447-3456]. This work represents the first biochemical example of the conversion of a phenol to an aniline.
• Synthesis of Phenol and Pyridone C-Ribo- and 2′-Deoxyribonucleosides by Palladium-Catalyzed Hydroxylations of Haloaryl C-Nucleosides
  作者：Michal Hocek、Martin Štefko

  DOI：10.1055/s-0030-1258318

  日期：2010.12

  Phenol and pyridone C-nucleosides in both ribo- and deoxyribo series were prepared by palladium-catalyzed hydroxylations reactions from the corresponding TBS-protected bromophenyl and bromo- or chloropyridyl C-nucleosides using Buchwald-type ligand under mild conditions. Partial or complete desilylation of 5′-OH was observed in some cases. Free nucleosides (7 examples) were obtained in good overall

  核糖和脱氧核糖系列中的苯酚和吡啶酮C-核苷是由钯催化的羟基化反应，由相应的TBS保护的溴苯基和溴或氯吡啶基C-核苷在温和条件下使用Buchwald型配体制备的。在某些情况下，观察到5'-OH的部分或完全甲硅烷基化。游离核苷（7个实施例）在由TBS保护基团用Et切割好的总产率得到3 N˙3HF。 C-核苷-钯催化-羟基化-苯酚-吡啶酮