(2S,3S,4S,5R)-2-benzyl-2,4-bis(hydroxymethyl)-3-methyl-5-phenyltetrahydrofuran | 1443117-65-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (2S,3S,4S,5R)-2-benzyl-2,4-bis(hydroxymethyl)-3-methyl-5-phenyltetrahydrofuran
• 英文别名: [(2R,3R,4S,5S)-5-benzyl-5-(hydroxymethyl)-4-methyl-2-phenyloxolan-3-yl]methanol
• CAS: 1443117-65-4
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: MYFDJBGCAATWIP-MVJPYGJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl 2-diazo-3-phenylpropanoate 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 rhodium(II) pivalate 、 nickel(II) tetrafluoroborate hexahydrate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 23.17h， 生成 (2S,3S,4S,5R)-2-benzyl-2,4-bis(hydroxymethyl)-3-methyl-5-phenyltetrahydrofuran
  参考文献：
  名称：

  Diastereoselective Synthesis of Tetrahydrofurans by Lewis Acid Catalyzed Intermolecular Carbenoid–Carbonyl Reaction–Cycloaddition Sequences: Unusual Diastereoselectivity of Lewis Acid Catalyzed Cycloadditions

  摘要：

  The effects of including metal salts for three. component reactions involving alpha-alkyl-alpha-diazo esters, aromatic aldehydes, and 3-(2-alkenoyl)-2-oxazolidinones are described, in terms of yields and diastereoselectivities. Metal tetrafluorborates (10-30 mol %) such as Co(BF4)(2)center dot 6H(2)O, Ni(BF4)(2)center dot 6H(2)O, and AgBF4 were effective in delivering high yields and diastereoselectivities (93:7 to 99:1) of the corresponding tetrahydrofuran derivatives while suppressing the competitive formation of 1,3-dioxolane. Using (S)-3-(2-alkenoyl)-4-isopropyl-2-oxazolidinones as the dipolarophiles in the three-component reactions, in the presence of Ni(BF4)(2)center dot 6H(2)O or Co(ClO4)(2)center dot 6H(2)O (10-30 mol %), optically active tetrahydrofurans that possess four successive asymmetric centers were synthesized in high diastereoselectivities (99:1). On the basis of the configuration of the cycloadduct using the X-ray analysis, the high diastereoselectivity could be explained by the unusual Re-face approach to the dipolarophile in the presence of the Lewis acid, proceeding through the s-cis conformer of the 3-(2-alkenoyl)-2-oxazolidinone with the two carbonyls in opposing directions (dipole-dipole interaction).

  DOI：

  10.1021/jo400858u

文献信息

• Diastereoselective Synthesis of Tetrahydrofurans by Lewis Acid Catalyzed Intermolecular Carbenoid–Carbonyl Reaction–Cycloaddition Sequences: Unusual Diastereoselectivity of Lewis Acid Catalyzed Cycloadditions
  作者：Yuta Hashimoto、Kennosuke Itoh、Akikazu Kakehi、Motoo Shiro、Hiroyuki Suga

  DOI：10.1021/jo400858u

  日期：2013.6.21

  The effects of including metal salts for three. component reactions involving alpha-alkyl-alpha-diazo esters, aromatic aldehydes, and 3-(2-alkenoyl)-2-oxazolidinones are described, in terms of yields and diastereoselectivities. Metal tetrafluorborates (10-30 mol %) such as Co(BF4)(2)center dot 6H(2)O, Ni(BF4)(2)center dot 6H(2)O, and AgBF4 were effective in delivering high yields and diastereoselectivities (93:7 to 99:1) of the corresponding tetrahydrofuran derivatives while suppressing the competitive formation of 1,3-dioxolane. Using (S)-3-(2-alkenoyl)-4-isopropyl-2-oxazolidinones as the dipolarophiles in the three-component reactions, in the presence of Ni(BF4)(2)center dot 6H(2)O or Co(ClO4)(2)center dot 6H(2)O (10-30 mol %), optically active tetrahydrofurans that possess four successive asymmetric centers were synthesized in high diastereoselectivities (99:1). On the basis of the configuration of the cycloadduct using the X-ray analysis, the high diastereoselectivity could be explained by the unusual Re-face approach to the dipolarophile in the presence of the Lewis acid, proceeding through the s-cis conformer of the 3-(2-alkenoyl)-2-oxazolidinone with the two carbonyls in opposing directions (dipole-dipole interaction).