(-)-(1Z)-{(4R,5R,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-6-hydroxy-4-methoxycyclohex-2-en-1-yliden}acetonitrile | 352426-56-3

• 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: (-)-(1Z)-{(4R,5R,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-6-hydroxy-4-methoxycyclohex-2-en-1-yliden}acetonitrile
• 英文别名: (2Z)-2-[(4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-4-methoxycyclohex-2-en-1-ylidene]acetonitrile
• CAS: 352426-56-3
• 化学式: C₁₅H₂₅NO₃Si
• 分子量: 295.454
• InChiKey: GNDHPKORXOUMCI-ZDCYIQFNSA-N

物化性质

• 沸点：
  388.6±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(1Z)-{(4R,5R,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-6-hydroxy-4-methoxycyclohex-2-en-1-yliden}acetonitrile 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以27%的产率得到(+)-(1E)-{(4R,5R,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-6-hydroxy-4-methoxycyclohex-2-en-1-yliden}acetonitrile
  参考文献：
  名称：

  Total Synthesis of (−)-Bauhinin

  摘要：

  The total synthesis of the naturally occurring cyanoglucoside (-)-bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (-)-bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig-Horner reaction followed by the opening of the oxa bridge. Glycosidation with tetra-O-isobutyryl-D-glucosyl bromide 9 as the reagent in the Koenigs-Knorr reaction afforded glucoside 10 in 58% yield, which, after photoisomerization and deprotection, gave (-)-bauhinin (1).

  DOI：

  10.1002/1522-2675(20010418)84:4<890::aid-hlca890>3.0.co;2-q
• 作为产物：
  描述：

  (2E,Z)-{(1S,4R,5R,6R)-6-endo-{[(tert-butyl)dimethylsilyl]oxy}-5-exo-methoxy-7-oxabicyclo[2.2.1]hept-2-yliden}acetonitrile 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以38%的产率得到(+)-(1E)-{(4R,5R,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-6-hydroxy-4-methoxycyclohex-2-en-1-yliden}acetonitrile
  参考文献：
  名称：

  Total Synthesis of (−)-Bauhinin

  摘要：

  The total synthesis of the naturally occurring cyanoglucoside (-)-bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (-)-bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig-Horner reaction followed by the opening of the oxa bridge. Glycosidation with tetra-O-isobutyryl-D-glucosyl bromide 9 as the reagent in the Koenigs-Knorr reaction afforded glucoside 10 in 58% yield, which, after photoisomerization and deprotection, gave (-)-bauhinin (1).

  DOI：

  10.1002/1522-2675(20010418)84:4<890::aid-hlca890>3.0.co;2-q