(5S,6R)-6-[(1S)-2-(tert-butyl-diphenylsilanyloxy)-1-methyl-ethyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol | 1033231-01-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (5S,6R)-6-[(1S)-2-(tert-butyl-diphenylsilanyloxy)-1-methyl-ethyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol
• CAS: 1033231-01-4
• 化学式: C₂₅H₃₄O₃Si
• 分子量: 410.629
• InChiKey: AKZZFISIYGMTNJ-NVXDSCFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5S,6R)-6-[(1S)-2-(tert-butyl-diphenylsilanyloxy)-1-methyl-ethyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol 、 异丙醇 在 对甲苯磺酸 作用下， 以82%的产率得到(1S)-tert-butyl-[(5S,6R)-2-(6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-propoxy]-diphenyl-silane
  参考文献：
  名称：

  Synthetic Studies toward C3‐C9 Segment of Soraphen A_1α

  摘要：

  The ring-closure metathesis of the diene (2S, 3R, 4S)-1-(tert-butyldiphenylsilyloxy)-2,4- dimethylhex-5-en-3-yl acrylate produced the dihydropyrone with the correct stereochemistry for Soraphen A(1 alpha) synthesis. The C2,C3 stereocenters were introduced by the addition of the (Z)-crotyl-n-butylstannane to the beta-alkoxyaldehyde( S)-3-(benzyloxy)-2-methylpropanal in presence of TiCl4 as a chelating catalyst to give the desired anti,syn homoallyic alcohol (2S, 3R, 4S)-1-(tert-butyldiphenylsilyloxy)2,4- dimethylhex-5-en-3-ol.

  DOI：

  10.1080/00397910801929358
• 作为产物：
  描述：

  (5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-5,6-dihydro-2H-pyran-2-one 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到(5S,6R)-6-[(1S)-2-(tert-butyl-diphenylsilanyloxy)-1-methyl-ethyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol
  参考文献：
  名称：

  Synthetic Studies toward C3‐C9 Segment of Soraphen A_1α

  摘要：

  The ring-closure metathesis of the diene (2S, 3R, 4S)-1-(tert-butyldiphenylsilyloxy)-2,4- dimethylhex-5-en-3-yl acrylate produced the dihydropyrone with the correct stereochemistry for Soraphen A(1 alpha) synthesis. The C2,C3 stereocenters were introduced by the addition of the (Z)-crotyl-n-butylstannane to the beta-alkoxyaldehyde( S)-3-(benzyloxy)-2-methylpropanal in presence of TiCl4 as a chelating catalyst to give the desired anti,syn homoallyic alcohol (2S, 3R, 4S)-1-(tert-butyldiphenylsilyloxy)2,4- dimethylhex-5-en-3-ol.

  DOI：

  10.1080/00397910801929358