(2S,3R,5E)-3-benzoyloxy-6-phenylhex-5-en-1,2-diol | 678148-78-2

• 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,3R,5E)-3-benzoyloxy-6-phenylhex-5-en-1,2-diol
• 英文别名: [(E,2S,3R)-1,2-dihydroxy-6-phenylhex-5-en-3-yl] benzoate
• CAS: 678148-78-2
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: HTRGPUJZDWLKIQ-INHTXZAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonate2-((S)-1-hydroxy-propyl)-phenyl-selenonium; 、 (2S,3R,5E)-3-benzoyloxy-6-phenylhex-5-en-1,2-diol 在 溴 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 Benzoic acid (2S,3R,5S,6R)-2-hydroxymethyl-5-[2-((S)-1-hydroxy-propyl)-phenylselanyl]-6-phenyl-tetrahydro-pyran-3-yl ester 、 Benzoic acid (2S,3R,5R,6S)-2-hydroxymethyl-5-[2-((S)-1-hydroxy-propyl)-phenylselanyl]-6-phenyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Diastereoselective Synthesis of Substituted 2-Phenyltetrahydropyrans as Useful Precursors of Aryl C-Glycosides via Selenoetherification

  摘要：

  The cyclization of several substituted 5-phenyl-pent-4-en-l-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.

  DOI：

  10.3987/com-03-9959
• 作为产物：
  描述：

  苯甲酸 、 (2S,3S,5E)-2,3-oxirane-6-phenylhex-5-en-1-ol 在 titanium(IV) isopropylate 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 以60%的产率得到(2S,3R,5E)-3-benzoyloxy-6-phenylhex-5-en-1,2-diol
  参考文献：
  名称：

  Diastereoselective Synthesis of Substituted 2-Phenyltetrahydropyrans as Useful Precursors of Aryl C-Glycosides via Selenoetherification

  摘要：

  The cyclization of several substituted 5-phenyl-pent-4-en-l-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.

  DOI：

  10.3987/com-03-9959

文献信息

• Diastereoselective Synthesis of Substituted 2-Phenyltetrahydropyrans as Useful Precursors of Aryl C-Glycosides via Selenoetherification
  作者：Michelangelo Gruttadauria、Carmela Aprile、Paolo Lo Meo、Serena Riela、Renato Noto

  DOI：10.3987/com-03-9959

  日期：——

  The cyclization of several substituted 5-phenyl-pent-4-en-l-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.