(1R,4R)-4-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-4-hydroxy-1-phenylbut-2-ynyl acetate | 914248-42-3

• 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: (1R,4R)-4-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-4-hydroxy-1-phenylbut-2-ynyl acetate
• CAS: 914248-42-3
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: JXKRPDNYTFHTST-USYVTKNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,4R)-4-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-4-hydroxy-1-phenylbut-2-ynyl acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以91%的产率得到(1R,2E,4S)-1-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-4-phenylbut-2-ene-1,4-diol
  参考文献：
  名称：

  1-Phenylprop-2-ynyl Acetate:  A Useful Building Block for the Stereoselective Construction of Polyhydroxylated Chains

  摘要：

  (R)- or (S)-1-phenylprop-2-ynyl acetate was added stereoselectively to aldehydes to afford 4-hydroxy-1-phenylalk-2-ynyl acetates. The transformation of such adducts into the corresponding allylic 1,4-diacetates allowed a highly efficient transfer of chirality from C1 to C3 by a regio- and stereoselective [3,3]-sigmatropic rearrangement. The obtained unsaturated 1,2-diacetates were useful synthetic intermediates whose double bond and/or phenyl group were transformed in different aldehydes, acids, or esters.

  DOI：

  10.1021/ol0616539
• 作为产物：
  描述：

  (S)-1-苯基-2-丙炔-1-醇 在 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 4.5h， 生成 (1R,4R)-4-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-4-hydroxy-1-phenylbut-2-ynyl acetate
  参考文献：
  名称：

  1-Phenylprop-2-ynyl Acetate:  A Useful Building Block for the Stereoselective Construction of Polyhydroxylated Chains

  摘要：

  (R)- or (S)-1-phenylprop-2-ynyl acetate was added stereoselectively to aldehydes to afford 4-hydroxy-1-phenylalk-2-ynyl acetates. The transformation of such adducts into the corresponding allylic 1,4-diacetates allowed a highly efficient transfer of chirality from C1 to C3 by a regio- and stereoselective [3,3]-sigmatropic rearrangement. The obtained unsaturated 1,2-diacetates were useful synthetic intermediates whose double bond and/or phenyl group were transformed in different aldehydes, acids, or esters.

  DOI：

  10.1021/ol0616539

文献信息

• New Stereoselective Approach to 1,2,3-Triols: Application to a Straight forward Access to Polyoxamic Acid Array
  作者：Xavier Ariza、Jordi Garcia、Jérémie Boyer、Yves Allenbach、Yohan Georges、Mar Vicente

  DOI：10.1055/s-2006-947361

  日期：2006.8

  An efficient approach to alk-4-yne-l,2,3,6-tetraols is described by stereoselective addition of terminal 2-alkyn-1-yl esters to Ley's butane-2,3-diacetal-protected glyceraldehyde. The application of this methodology to a convenient synthesis of (-)-polyoxamic acid derivative is disclosed herein.

  alk-4-yne-1,2,3,6-tetraols 的有效方法是通过立体选择性加成末端 2-alkyn-1-yl 酯到 Ley's 丁烷-2,3-二缩醛保护的甘油醛。本文公开了该方法在(-)-聚肟酸衍生物的方便合成中的应用。