[(1S,2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol | 198822-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: [(1S,2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol
• CAS: 198822-20-7
• 化学式: C₁₄H₂₆O₃Si
• 分子量: 270.444
• InChiKey: PXMRMDWUQBZPOK-MROQNXINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  [(1S,2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol 在 吡啶 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 戴斯-马丁氧化剂 、 tetramethylammonium triacetoxyborohydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 30.75h， 生成
  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 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以99%的产率得到[(1S,2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol
  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