[(2R,3S)-3-[[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxymethyl)oxiran-2-yl]methanol | 190896-37-8

• 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: [(2R,3S)-3-[[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxymethyl)oxiran-2-yl]methanol
• CAS: 190896-37-8
• 化学式: C₂₀H₃₄O₄Si
• 分子量: 366.573
• InChiKey: YHQOLXCYAXEGCX-QUCCMNQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-3-[[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxymethyl)oxiran-2-yl]methanol 在 copper(l) iodide 、 4-甲基苯磺酸吡啶 、 lithium 作用下， 以 四氢呋喃 、 乙醚 、 氨 为溶剂， 反应 24.17h， 生成 {(4S,5S)-4-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-methanol
  参考文献：
  名称：

  Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes

  摘要：

  Two chiral quaternary carbon-containing fragments suitable for elaboration to the briaran diterpenes were obtained by regioselective methylation of functionalized 3,3-disubstituted 2,3-epoxy-1-ols. The factors which favor methylation at the more hindered position of a trisubstituted 2.3-epoxy alcohol were determined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00453-5
• 作为产物：
  描述：

  4-hydroxymethyl-5H-furan-2-one 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 正丁基锂 、 D-(-)-酒石酸二乙酯 、 三氟甲磺酸 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 异辛烷 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.84h， 生成 [(2R,3S)-3-[[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxymethyl)oxiran-2-yl]methanol
  参考文献：
  名称：

  Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes

  摘要：

  Two chiral quaternary carbon-containing fragments suitable for elaboration to the briaran diterpenes were obtained by regioselective methylation of functionalized 3,3-disubstituted 2,3-epoxy-1-ols. The factors which favor methylation at the more hindered position of a trisubstituted 2.3-epoxy alcohol were determined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00453-5

文献信息

• Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes
  作者：Rajiv P. Balasubramaniam、David K. Moss、Justin K. Wyatt、John D. Spence、Arvin Gee、Michael H. Nantz

  DOI：10.1016/s0040-4020(97)00453-5

  日期：1997.6

  Two chiral quaternary carbon-containing fragments suitable for elaboration to the briaran diterpenes were obtained by regioselective methylation of functionalized 3,3-disubstituted 2,3-epoxy-1-ols. The factors which favor methylation at the more hindered position of a trisubstituted 2.3-epoxy alcohol were determined. (C) 1997 Elsevier Science Ltd.