(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-2,5-dimethyl-3-cyclohexene-1-carboxaldehyde | 427897-79-8

• 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: (1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-2,5-dimethyl-3-cyclohexene-1-carboxaldehyde
• 英文别名: (1S,2S,5S)-2-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-hydroxy-2,5-dimethylcyclohex-3-ene-1-carbaldehyde
• CAS: 427897-79-8
• 化学式: C₃₅H₅₄O₄Si₂
• 分子量: 594.982
• InChiKey: YEHYOSNHFGPUJQ-JCXRYELGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.27
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-2,5-dimethyl-3-cyclohexene-1-carboxaldehyde 在 氢氧化钾 、 碘 、 二异丁基氢化铝 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 生成 (+/-)-methyl (1S,2S,5S)-1-acetoxy-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,5-dimethyl-2-(3-hydroxypropyl)-3-cyclohexene-1-carboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of the endo- and exo-Spirotetronate Subunits of the Quartromicins. The First Enantioselective Diels−Alder Reaction of an Acyclic (Z)-1,3-Diene

  摘要：

  Diastereoselective syntheses of the endo- and exo-spirotetronates 1 and 2, corresponding to the galacto and agalacto fragments of quartromicins A(3) and D-3, are described. The key step of these syntheses are highly enantio- and diastereoselective Lewis acid catalyzed Diels-Alder reactions of the 1,1,3,4-tetrasubstituted diene 3.

  DOI：

  10.1021/ol025772+
• 作为产物：
  描述：

  (1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethyl-3-cyclohexene-1-carboxaldehyde 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-2,5-dimethyl-3-cyclohexene-1-carboxaldehyde
  参考文献：
  名称：

  Diastereoselective Synthesis of the endo- and exo-Spirotetronate Subunits of the Quartromicins. The First Enantioselective Diels−Alder Reaction of an Acyclic (Z)-1,3-Diene

  摘要：

  Diastereoselective syntheses of the endo- and exo-spirotetronates 1 and 2, corresponding to the galacto and agalacto fragments of quartromicins A(3) and D-3, are described. The key step of these syntheses are highly enantio- and diastereoselective Lewis acid catalyzed Diels-Alder reactions of the 1,1,3,4-tetrasubstituted diene 3.

  DOI：

  10.1021/ol025772+

文献信息

• Studies on the synthesis of the quartromicins: partial stereochemical assignment of quartromicins A3 and D3 and diastereoselective synthesis of the endo- and exo-spirotetronate subunits
  作者：William R Roush、David A Barda、Chris Limberakis、Roxanne K Kunz

  DOI：10.1016/s0040-4020(02)00656-7

  日期：2002.8

  A partial stereochemical assignment of quartromicins A3 and D3 is presented, along with diastereoselective syntheses of the endo- and exo-spirotetronates 1 and 2, corresponding to the galacto and agalacto fragments of the proposed quartromicin stereostructure. The key steps of these syntheses are highly enantio- and diastereoselective Lewis acid catalyzed Diels–Alder reactions of 1,1,3,4-tetrasubstituted

  quartromicins A的局部立体化学指定3和d 3被呈现，用非对映选择性合成沿着内切-和外切-spirotetronates 1和2中，对应于半乳糖和agalacto拟议quartromicin立体的片段。这些合成的关键步骤是高度对映体和非对映体选择性路易斯酸催化1,1,3,4-四取代的二烯24的Diels-Alder反应。