(R)-phenyl((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methanol | 1028182-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-phenyl((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methanol
• 英文别名: (1R)-O²,O³;O⁴,O⁵-diisopropylidene-1-phenyl-D-arabitol；(1R)-O²,O³;O⁴,O⁵-Diisopropyliden-1-phenyl-D-arabit；(R)-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethanol
• CAS: 1028182-40-2
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: MCYPLHQSLQNUIE-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-phenyl((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methanol 在 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以91%的产率得到phenyl((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)-methanone
  参考文献：
  名称：

  Total synthesis of 8-methoxygoniodiol related compounds via chiron approach

  摘要：

  The stereoselective synthesis of 8-methoxygoniodiol related compounds was accomplished by using readily available delta-gluconolactone as a chiral source. The stereoselective addition of an aryl Grignard reagent on an aldehyde, stereoselective reduction of a keto group and regioselective opening of a chiral epoxide by ethyl propiolate are the key steps involved in this synthesis. (c) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.05.034
• 作为产物：
  描述：

  溴苯 、 2,3-二氟-6-硝基苯胺 在 magnesium 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到(R)-phenyl((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methanol
  参考文献：
  名称：

  Total synthesis of 8-methoxygoniodiol related compounds via chiron approach

  摘要：

  The stereoselective synthesis of 8-methoxygoniodiol related compounds was accomplished by using readily available delta-gluconolactone as a chiral source. The stereoselective addition of an aryl Grignard reagent on an aldehyde, stereoselective reduction of a keto group and regioselective opening of a chiral epoxide by ethyl propiolate are the key steps involved in this synthesis. (c) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.05.034

文献信息

• Total Synthesis of 8-Methoxygoniodiol via Chiron Approach
  作者：J. Yadav、B. Rao、K. Sanjeevarao、B. Reddy

  DOI：10.1055/s-2008-1072511

  日期：——

  A stereoselective synthesis of 8-methoxygoniodiol is accomplished using readily available δ-gluconolactone as a chiral source. The stereoselective addition of aryl Grignard reagent on aldehyde and regioselective opening of chiral epoxide by ethyl propiolate are the key steps involved in this synthesis.

  使用现成的 δ-葡糖酸内酯作为手性来源，完成了 8-甲氧基角二醇的立体选择性合成。芳基格氏试剂在醛上的立体选择性加成和丙炔酸乙酯对手性环氧化物的区域选择性打开是该合成中涉及的关键步骤。
• The Stereochemical Configurations of the 1-C-Phenyl-D-pentitols
  作者：William A. Bonner

  DOI：10.1021/ja01151a038

  日期：1951.7