(2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-3-hydroxy-6-(hydroxymethyl)-2-methoxy-1,2-oxaphosphinane 2-oxide | 1445800-51-0

• 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)-4,5-bis(benzyloxy)-3-hydroxy-6-(hydroxymethyl)-2-methoxy-1,2-oxaphosphinane 2-oxide
• 英文别名: (2R,3S,4S,5S,6R)-6-(hydroxymethyl)-2-methoxy-2-oxo-4,5-bis(phenylmethoxy)-1,2lambda5-oxaphosphinan-3-ol；(2R,3S,4S,5S,6R)-6-(hydroxymethyl)-2-methoxy-2-oxo-4,5-bis(phenylmethoxy)-1,2λ5-oxaphosphinan-3-ol
• CAS: 1445800-51-0
• 化学式: C₂₀H₂₅O₇P
• 分子量: 408.388
• InChiKey: DALDIWHSDRTQEX-GREGNEDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  triethylammonium (2S,3S,4S,5S,6R)-2-borane-3-acetoxy-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-1,2-oxaphosphinan-2-olate 、 (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-3-hydroxy-6-(hydroxymethyl)-2-methoxy-1,2-oxaphosphinane 2-oxide 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 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-3-hydroxy-2-methoxy-2-oxido-1,2-oxaphosphinan-6-yl)methoxy)-2-oxido-1,2-oxaphosphinan-3-yl 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
• 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 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 31.0h， 生成 (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-3-hydroxy-6-(hydroxymethyl)-2-methoxy-1,2-oxaphosphinane 2-oxide
  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