(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-3-ol | 195004-90-1

• 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: (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-3-ol
• 英文别名: (2S,3S,4S,5R)-2-methoxy-2-oxo-4,5-bis(phenylmethoxy)-1,2lambda5-oxaphosphinan-3-ol；(2S,3S,4S,5R)-2-methoxy-2-oxo-4,5-bis(phenylmethoxy)-1,2λ5-oxaphosphinan-3-ol
• CAS: 195004-90-1
• 化学式: C₁₉H₂₃O₆P
• 分子量: 378.362
• InChiKey: RRKLJQBJWVFBOF-KSSHPSMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 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：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-3-ol 在 盐酸 、 三甲基溴硅烷 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 反应 3.75h， 生成 (2S,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-2-ol
  参考文献：
  名称：

  Synthesis of Cyclic Phosphonate Analogs of Ribose and Arabinose

  摘要：

  The cyclic phosphonates of ribose and arabinose (phostones) 10-13 were synthesized by a Lewis acid-catalyzed addition of trimethyl phosphite to the partially protected D-threose 7 to give the acyclic phosphonates 8 and 9, This Abramov reaction was moderately stereoselective (3:1). A base-catalyzed cyclization of the mixture of 8 and 9 gave the four isomeric phosphonates 10-13, Two of the isomers, 10 and 11, could be crystallized from the reaction mixture, The stereochemistries of 11 and 16, the tribenzyl ether from 10, were proven by X-ray crystallography, and the stereochemistries of the other isomers and derivatives were determined by P-31 NMR chemical shift data, The X-ray data and solution NMR data indicate that these phostones and their derivatives exist exclusively in a chair conformation.

  DOI：

  10.1021/jo9706382
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以19%的产率得到(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-3-ol
  参考文献：
  名称：

  Synthesis of Cyclic Phosphonate Analogs of Ribose and Arabinose

  摘要：

  The cyclic phosphonates of ribose and arabinose (phostones) 10-13 were synthesized by a Lewis acid-catalyzed addition of trimethyl phosphite to the partially protected D-threose 7 to give the acyclic phosphonates 8 and 9, This Abramov reaction was moderately stereoselective (3:1). A base-catalyzed cyclization of the mixture of 8 and 9 gave the four isomeric phosphonates 10-13, Two of the isomers, 10 and 11, could be crystallized from the reaction mixture, The stereochemistries of 11 and 16, the tribenzyl ether from 10, were proven by X-ray crystallography, and the stereochemistries of the other isomers and derivatives were determined by P-31 NMR chemical shift data, The X-ray data and solution NMR data indicate that these phostones and their derivatives exist exclusively in a chair conformation.

  DOI：

  10.1021/jo9706382

文献信息

• Synthesis of Cyclic Phosphonate Analogs of Ribose and Arabinose
  作者：Thomas C. Harvey、Cécile Simiand,、Larry Weiler、Stephen G. Withers

  DOI：10.1021/jo9706382

  日期：1997.10.1

  The cyclic phosphonates of ribose and arabinose (phostones) 10-13 were synthesized by a Lewis acid-catalyzed addition of trimethyl phosphite to the partially protected D-threose 7 to give the acyclic phosphonates 8 and 9, This Abramov reaction was moderately stereoselective (3:1). A base-catalyzed cyclization of the mixture of 8 and 9 gave the four isomeric phosphonates 10-13, Two of the isomers, 10 and 11, could be crystallized from the reaction mixture, The stereochemistries of 11 and 16, the tribenzyl ether from 10, were proven by X-ray crystallography, and the stereochemistries of the other isomers and derivatives were determined by P-31 NMR chemical shift data, The X-ray data and solution NMR data indicate that these phostones and their derivatives exist exclusively in a chair conformation.