(R)-4,4-dimethyl-1,3-dioxane-5-methanol | 146727-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (R)-4,4-dimethyl-1,3-dioxane-5-methanol
• 英文别名: [(5R)-4,4-dimethyl-1,3-dioxan-5-yl]methanol
• CAS: 146727-88-0
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: CLOFLDZIKBYHST-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4,4-dimethyl-1,3-dioxane-5-methanol 在 disodium hydrogenphosphate 、 sodium amalgam 、 二甲基溴化硼 、 三丁基膦 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.5h， 生成 <<(1α,3β,5E,7E,22E)-25,28-<(1-methylethylidene)bis(oxy)>-9,10-secoergosta-5,7,10(19),22-tetraene-1,3-diyl>bis(oxy)>bis<(1,1-dimethylethyl)dimethylsilane>
  参考文献：
  名称：

  Synthesis of a biologically active vitamin D2 metabolite

  摘要：

  The synthesis of 1alpha,25,28-trihydroxyvitamin-D2 (1) from vitamin-D2 is described. Approaches to the upper side-chain synthon via the chiral sulfone 15, prepared either through the enzymatic resolution of 10 or the opening of the optically pure epoxide 17 with the dianion of methyl phenyl sulfone, are described. A Julia coupling of the sulfone 15 with C-1 hydroxylated aldehyde 7, obtained from vitamin-D2, gave the (22E)-isomer 24a, which was deprotected and photoisomerized to give 1.

  DOI：

  10.1021/jo00058a034
• 作为产物：
  描述：

  (4,4-二甲基-1,3-二恶烷-5-基)甲醇 在 乙酸乙烯酯 作用下， 反应 8.5h， 以26%的产率得到(R)-4,4-dimethyl-1,3-dioxane-5-methanol
  参考文献：
  名称：

  Synthesis of a biologically active vitamin D2 metabolite

  摘要：

  The synthesis of 1alpha,25,28-trihydroxyvitamin-D2 (1) from vitamin-D2 is described. Approaches to the upper side-chain synthon via the chiral sulfone 15, prepared either through the enzymatic resolution of 10 or the opening of the optically pure epoxide 17 with the dianion of methyl phenyl sulfone, are described. A Julia coupling of the sulfone 15 with C-1 hydroxylated aldehyde 7, obtained from vitamin-D2, gave the (22E)-isomer 24a, which was deprotected and photoisomerized to give 1.

  DOI：

  10.1021/jo00058a034

文献信息

• Synthesis of a biologically active vitamin D2 metabolite
  作者：Satish C. Choudhry、Peter S. Belica、David L. Coffen、Antonino Focella、Hubert Maehr、Percy S. Manchand、Lucia Serico、Roxana T. Yang

  DOI：10.1021/jo00058a034

  日期：1993.3

  The synthesis of 1alpha,25,28-trihydroxyvitamin-D2 (1) from vitamin-D2 is described. Approaches to the upper side-chain synthon via the chiral sulfone 15, prepared either through the enzymatic resolution of 10 or the opening of the optically pure epoxide 17 with the dianion of methyl phenyl sulfone, are described. A Julia coupling of the sulfone 15 with C-1 hydroxylated aldehyde 7, obtained from vitamin-D2, gave the (22E)-isomer 24a, which was deprotected and photoisomerized to give 1.