[(2R,3R)-2-[(2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyloxiran-2-yl]hexan-3-yl] methanesulfonate | 237066-78-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [(2R,3R)-2-[(2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyloxiran-2-yl]hexan-3-yl] methanesulfonate
• CAS: 237066-78-3
• 化学式: C₁₇H₃₆O₅SSi
• 分子量: 380.621
• InChiKey: VPCBNRZAEHKTDP-IVSAIRAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,3R)-2-[(2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyloxiran-2-yl]hexan-3-yl] methanesulfonate 、 三氟甲磺酸三甲基硅酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以70%的产率得到[(4R,5R,6S,7R)-5,7-dimethyl-8-oxo-6-trimethylsilyloxyoctan-4-yl] methanesulfonate
  参考文献：
  名称：

  Synthesis of Four Diastereomeric 3,5-Dialkoxy-2,4-dimethylalkanals by a Simple Extension of the Non-Aldol Aldol Process to Bis(propionates)

  摘要：

  [GRAPHICS]The synthesis of all four diastereomers of bis(propionates), 3,5-dialkoxy-2,4-dimethylalkanals, by non-aldol aldol chemistry is described. The epoxy alcohols (3, 4) were converted into the mesylates (9, 11) which were cleanly rearranged to the desired 3,5-bis(oxygenated)-2,4 dimethylalkanals (10, 12) in high yield. The epoxy mesylates (13, 16) gave the desired products (14, 17) in good yield on treatment with TMSOTf and a hindered base.

  DOI：

  10.1021/ol990619+
• 作为产物：
  描述：

  [(2S,3S)-2-methyl-3-[(2R,3R)-3-triethylsilyloxyhexan-2-yl]oxiran-2-yl]methanol 在 四丁基氟化铵 作用下， 生成 [(2R,3R)-2-[(2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyloxiran-2-yl]hexan-3-yl] methanesulfonate
  参考文献：
  名称：

  Synthesis of Four Diastereomeric 3,5-Dialkoxy-2,4-dimethylalkanals by a Simple Extension of the Non-Aldol Aldol Process to Bis(propionates)

  摘要：

  [GRAPHICS]The synthesis of all four diastereomers of bis(propionates), 3,5-dialkoxy-2,4-dimethylalkanals, by non-aldol aldol chemistry is described. The epoxy alcohols (3, 4) were converted into the mesylates (9, 11) which were cleanly rearranged to the desired 3,5-bis(oxygenated)-2,4 dimethylalkanals (10, 12) in high yield. The epoxy mesylates (13, 16) gave the desired products (14, 17) in good yield on treatment with TMSOTf and a hindered base.

  DOI：

  10.1021/ol990619+

文献信息

• Synthesis of Four Diastereomeric 3,5-Dialkoxy-2,4-dimethylalkanals by a Simple Extension of the Non-Aldol Aldol Process to Bis(propionates)
  作者：Michael E. Jung、Woo Song Lee、Daqing Sun

  DOI：10.1021/ol990619+

  日期：1999.7.1

  [GRAPHICS]The synthesis of all four diastereomers of bis(propionates), 3,5-dialkoxy-2,4-dimethylalkanals, by non-aldol aldol chemistry is described. The epoxy alcohols (3, 4) were converted into the mesylates (9, 11) which were cleanly rearranged to the desired 3,5-bis(oxygenated)-2,4 dimethylalkanals (10, 12) in high yield. The epoxy mesylates (13, 16) gave the desired products (14, 17) in good yield on treatment with TMSOTf and a hindered base.