(2R,3S)-1,3-diphenylmethoxy-2,6-hexanediol | 223575-40-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S)-1,3-diphenylmethoxy-2,6-hexanediol
• 英文别名: (4S,5R)-4,6-bis(benzyloxy)hexane-1,5-diol；(4S,5R)-4,6-bis(phenylmethoxy)hexane-1,5-diol
• CAS: 223575-40-4
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: QDOYGHTWTVSOPV-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1,3-diphenylmethoxy-2,6-hexanediol 在 吡啶 、 盐酸 、 草酰氯 、 甲基锂 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 90.0h， 生成 (6S,7R,E)-7-hydroxy-3-methyl-6,8-diphenylmethoxy-2-octanoic acid ethyl ester
  参考文献：
  名称：

  Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center

  摘要：

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.

  DOI：

  10.1021/jo9822380
• 作为产物：
  描述：

  (4S,5R,E)-4,6-bis(benzyloxy)hex-2-ene-1,5-diol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.33h， 以73%的产率得到(2R,3S)-1,3-diphenylmethoxy-2,6-hexanediol
  参考文献：
  名称：

  由d-甘醇合成（-）-脱氧脯氨酸，（+）-2-表-脱氧胸苷，以及（2 R，3 R）-和（2 R，3 S）-3-羟基哌酸

  摘要：

  报道了（-）-脱氧脯氨酸，（+）-2-表-脱氧胸苷，（2 R，3 R）-和（2 R，3 S）-3-羟基哌酸的新合成。衍生自3,4,6- tri - O-苄基缩醛的Perlin醛的手性官能团已被用作主要步骤，同时对烯烃进行了化学选择性饱和和还原性胺化反应。

  DOI：

  10.1021/jo100489k

文献信息

• Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center
  作者：Qiang Zhu、Li-Xin Qiao、Yikang Wu、Yu-Lin Wu

  DOI：10.1021/jo9822380

  日期：1999.4.1

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.
• Synthesis of (−)-Deoxoprosophylline, (+)-2-<i>epi</i>-Deoxoprosopinine, and (2<i>R</i>,3<i>R</i>)- and (2<i>R</i>,3<i>S</i>)-3-Hydroxypipecolic Acids from <scp>d</scp>-Glycals
  作者：Hari Prasad Kokatla、Rima Lahiri、Pavan K. Kancharla、Venkata Ramana Doddi、Yashwant D. Vankar

  DOI：10.1021/jo100489k

  日期：2010.7.2

  New syntheses of (−)-deoxoprosophylline, (+)-2-epi-deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids are reported. Utilization of the chiral functionalities of Perlin aldehydes, derived from 3,4,6-tri-O-benzyl glycals, has been done along with chemoselective saturation of olefins and reductive aminations as key steps.

  报道了（-）-脱氧脯氨酸，（+）-2-表-脱氧胸苷，（2 R，3 R）-和（2 R，3 S）-3-羟基哌酸的新合成。衍生自3,4,6- tri - O-苄基缩醛的Perlin醛的手性官能团已被用作主要步骤，同时对烯烃进行了化学选择性饱和和还原性胺化反应。