(2S,6R)-2-(2-Benzyloxy-ethyl)-6-((R)-toluene-4-sulfinylmethyl)-tetrahydro-pyran | 148905-66-2

• 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,6R)-2-(2-Benzyloxy-ethyl)-6-((R)-toluene-4-sulfinylmethyl)-tetrahydro-pyran
• 英文别名: (2R,6S)-2-[[(R)-(4-methylphenyl)sulfinyl]methyl]-6-(2-phenylmethoxyethyl)oxane
• CAS: 148905-66-2
• 化学式: C₂₂H₂₈O₃S
• 分子量: 372.529
• InChiKey: SRZRUBFZHGDGJY-LZCXECNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,6R)-2-(2-Benzyloxy-ethyl)-6-((R)-toluene-4-sulfinylmethyl)-tetrahydro-pyran 在 lithium aluminium tetrahydride 、 sodium acetate 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (2S,6S)-2-(2-Benzyloxy-ethyl)-6-methyl-tetrahydro-pyran
  参考文献：
  名称：

  A highly stereoselective synthetic method for cis-2- hydroxymethyl-6-alkyltetrahydropyrans

  摘要：

  A highly stereoselective synthetic method for cis-2-hydroxymethyl 6-alkyltetrahydropyrans is described by an intramolecular 1,4-addition of alcohol to alpha,beta-unsaturated sulfoxide as a key reaction. This method is applied to syntheses of (+) and (-)-(cis-6-methyltetrahydropyran-2-yl)acetic acid.

  DOI：

  10.1016/s0040-4039(00)60070-9
• 作为产物：
  描述：

  [(E)-1-(2-Benzyloxy-ethyl)-6-((R)-toluene-4-sulfinyl)-hex-5-enyloxy]-tert-butyl-dimethyl-silane 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以45.2%的产率得到(2S,6R)-2-(2-Benzyloxy-ethyl)-6-((R)-toluene-4-sulfinylmethyl)-tetrahydro-pyran
  参考文献：
  名称：

  A highly stereoselective synthetic method for cis-2- hydroxymethyl-6-alkyltetrahydropyrans

  摘要：

  A highly stereoselective synthetic method for cis-2-hydroxymethyl 6-alkyltetrahydropyrans is described by an intramolecular 1,4-addition of alcohol to alpha,beta-unsaturated sulfoxide as a key reaction. This method is applied to syntheses of (+) and (-)-(cis-6-methyltetrahydropyran-2-yl)acetic acid.

  DOI：

  10.1016/s0040-4039(00)60070-9

文献信息

• A highly stereoselective synthetic method for cis-2- hydroxymethyl-6-alkyltetrahydropyrans
  作者：Tadakatsu Mandai、Masayuki Ueda、Kaori Kashiwagi、Mikio Kawada、Jiro Tsuji

  DOI：10.1016/s0040-4039(00)60070-9

  日期：1993.1

  A highly stereoselective synthetic method for cis-2-hydroxymethyl 6-alkyltetrahydropyrans is described by an intramolecular 1,4-addition of alcohol to alpha,beta-unsaturated sulfoxide as a key reaction. This method is applied to syntheses of (+) and (-)-(cis-6-methyltetrahydropyran-2-yl)acetic acid.