tert-Butyl-[(1R,2R,3S,4S)-3-((4R,6S)-2,2-dimethyl-6-propyl-[1,3]dioxan-4-yl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethoxy]-dimethyl-silane | 198822-24-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: tert-Butyl-[(1R,2R,3S,4S)-3-((4R,6S)-2,2-dimethyl-6-propyl-[1,3]dioxan-4-yl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethoxy]-dimethyl-silane
• CAS: 198822-24-1
• 化学式: C₂₂H₄₀O₄Si
• 分子量: 396.643
• InChiKey: UUTPFFQHHGMTMQ-IEJRGFGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl-[(1R,2R,3S,4S)-3-((4R,6S)-2,2-dimethyl-6-propyl-[1,3]dioxan-4-yl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethoxy]-dimethyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到(1S,2S,3R,4R,1'R,3'S)-2-(4',6'-dioxa-5',5'-dimethyl-3'-propylcyclohexyl)-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  A novel and efficient stereoselective synthesis of the southern part of pamamycin-607

  摘要：

  The C1'C11' portion of the antibiotic pamamycin-607 Was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute configurations of C-6' and C-8' were fixed by an aldol condensation followed by an anti-reduction of the resulting beta-hydroxyketone. The configurations of the last two asymmetric centers C-2' and C-3' were controlled by a novel highly diastereoselective intramolecular cyclization catalyzed by fluoride ions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00475-8
• 作为产物：
  描述：

  Acetic acid (1S,2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 在 氢氧化钾 、 4-甲基苯磺酸吡啶 、 戴斯-马丁氧化剂 、 tetramethylammonium triacetoxyborohydride 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 23.5h， 生成 tert-Butyl-[(1R,2R,3S,4S)-3-((4R,6S)-2,2-dimethyl-6-propyl-[1,3]dioxan-4-yl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethoxy]-dimethyl-silane
  参考文献：
  名称：

  A novel and efficient stereoselective synthesis of the southern part of pamamycin-607

  摘要：

  The C1'C11' portion of the antibiotic pamamycin-607 Was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute configurations of C-6' and C-8' were fixed by an aldol condensation followed by an anti-reduction of the resulting beta-hydroxyketone. The configurations of the last two asymmetric centers C-2' and C-3' were controlled by a novel highly diastereoselective intramolecular cyclization catalyzed by fluoride ions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00475-8