((2R,3S,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-1,2-oxaphosphinan-6yl)methyl acetate | 1384982-07-3

• 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,3S,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-1,2-oxaphosphinan-6yl)methyl acetate
• CAS: 1384982-07-3
• 化学式: C₂₄H₂₉O₉P
• 分子量: 492.463
• InChiKey: MDGMHJGKBJXYNQ-GHRDIZJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ((2R,3S,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-1,2-oxaphosphinan-6yl)methyl acetate 在 4-二甲氨基吡啶 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Alternative Synthesis of P-Chiral Phosphonite-Borane Complexes: Application to the Synthesis of Phostone–Phostone Dimers

  摘要：

  An improved strategy for the synthesis of P-chiral gluco- and manno-phosphonite-borane complexes is described on the basis of the addition of diethyl phosphonite-borane to a glucal-derived aldehyde, followed by a cyclization coupled with an ethyl/methyl exchange. This direct P(III) strategy facilitates the obtention of various P-chiral phosphonite-boranes, of which further coupling reactions are described leading to the selective synthesis of two phostone dimers.

  DOI：

  10.1021/jo400864s
• 作为产物：
  描述：

  (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-oxido-1,2-oxaphosphinan-3yl acetate 、 乙酸酐 在 三氟乙酸 作用下， 反应 7.0h， 以100%的产率得到((2R,3S,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-1,2-oxaphosphinan-6yl)methyl acetate
  参考文献：
  名称：

  Alternative Synthesis of P-Chiral Phosphonite-Borane Complexes: Application to the Synthesis of Phostone–Phostone Dimers

  摘要：

  An improved strategy for the synthesis of P-chiral gluco- and manno-phosphonite-borane complexes is described on the basis of the addition of diethyl phosphonite-borane to a glucal-derived aldehyde, followed by a cyclization coupled with an ethyl/methyl exchange. This direct P(III) strategy facilitates the obtention of various P-chiral phosphonite-boranes, of which further coupling reactions are described leading to the selective synthesis of two phostone dimers.

  DOI：

  10.1021/jo400864s

文献信息

• Synthesis, Characterization, and Coupling Reactions of Six-Membered Cyclic P-Chiral Ammonium Phosphonite–Boranes; Reactive <i>H</i>-Phosphinate Equivalents for the Stereoselective Synthesis of Glycomimetics
  作者：Angélique Ferry、Xavier Guinchard、Pascal Retailleau、David Crich

  DOI：10.1021/ja305104b

  日期：2012.7.25

  phostone-mimetics of disaccharides. On the basis of these studies, successful protocols were established for the synthesis of β-gluco and α- and β-manno-configured phostones of primary alcohols. Deprotection of the dimeric compounds leads to novel families of α- or β-(1→6)-linked glycomimetics.

  葡萄糖和甘露糖系列中 P-手性亚膦酸铵-硼烷配合物的立体选择性合成已从 P(V) 膦衍生物发展而来。已经研究了这些光酮供体与醇的偶联反应，特别强调保护基团和条件对立体选择性的影响。亚膦酸酯-硼烷复合物可直接用于偶联反应，产物原位氧化以得到二糖的磷酮模拟物。在这些研究的基础上，建立了合成 β-葡萄糖和 α- 和 β- 甘露糖构型伯醇的成功方案。二聚体化合物的去保护导致了新的α-或β-(1→6)-连接的糖模拟物家族。