2,5-dibenzyloxy-1-hydroxy-3-hydroxy-β-D-ribose | 1583259-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dibenzyloxy-1-hydroxy-3-hydroxy-β-D-ribose
• 英文别名: (2R,3R,4R,5R)-3-phenylmethoxy-5-(phenylmethoxymethyl)oxolane-2,4-diol
• CAS: 1583259-13-5
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: HWTOVHZZFOYLLB-NCXUSEDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-苄氧基-1-丙醇 在 二异丙氧基二氯化钛 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid 、 水 、 溶剂黄146 、 copper dichloride 、 锌 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 76.0h， 生成 2,5-dibenzyloxy-1-hydroxy-3-hydroxy-α-D-ribose 、 2,5-dibenzyloxy-1-hydroxy-3-hydroxy-β-D-ribose
  参考文献：
  名称：

  A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir

  摘要：

  An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective alpha-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

  DOI：

  10.1021/ja502205q

文献信息

• EP0565590A4
  申请人：——

  公开号：EP0565590A4

  公开（公告）日：1995-07-05
• ADHESIN-OLIGOSACCHARIDE CONJUGATE VACCINE FOR $i(HAEMOPHILUS INFLUENZAE)
  申请人：MicroCarb Inc.

  公开号：EP0565590A1

  公开（公告）日：1993-10-20
• [EN] ADHESIN-OLIGOSACCHARIDE CONJUGATE VACCINE FOR HAEMOPHILUS INFLUENZAE
  申请人：MICROCARB, INC.

  公开号：WO1992010936A1

  公开（公告）日：1992-07-09

  (EN) Disclosed herein are immunogenic polysaccharide-$i(H. influenzae) adhesin protein conjugates, a purified $i(H. influenzae) adhesin protein and related proteins and polypeptides, DNA useful for producing the proteins, synthetic polyribosylribotol phosphate (PRP) oligosaccharides and intermediates useful for their synthesis, and methods of making and using these materials. The conjugates comprise a PRP fragment, preferably a synthetic oligosaccharide, coupled to an $i(H. influenzae) adhesin protein. The invention further comprises purified $i(H. influenzae) adhesin proteins and novel PRP oligosaccharides. The invention also comprises methods of producing these materials and using them in a vaccine to protect humans and other mammals against $i(H. influenzae) infection.(FR) L'invention décrit des conjugués de protéines adhésines et de polysaccharides de $i(H. influenzae) immunogènes, une protéine adhésine de $i(H. influenzae) purifiée, ainsi que les protéines et polypeptides apparentés, l'ADN utilisé dans la production des protéines, les oligosaccharides synthétiques de phosphate de polyribosylribotol (PRP) ainsi que les intermédiaires utilisés dans leur synthèse, et les procédés de production et d'utilisation desdits produits. Les conjugués comprennent un fragment de PRP, de préférence un oligosaccharide synthétique, couplé à une protéine adhésive de $i(H. influenzae). L'invention se rapporte, de plus, à des protéines adhésines de $i(H. influenzae) purifiées et à de nouveaux oligosaccharides de PEP. L'invention comprend également des procédés de fabrication desdits produits, ainsi que leur utilisation comme vaccins servant à la protection des humains et autres mammifères contre l'infection par $i(H. influenzae).
• A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir
  作者：Manuel Peifer、Raphaëlle Berger、Valerie W. Shurtleff、Jay C. Conrad、David W. C. MacMillan

  DOI：10.1021/ja502205q

  日期：2014.4.23

  An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective alpha-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.