(+)-(1E)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile | 352426-53-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (+)-(1E)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile
• 英文别名: [(2R,3R,4S,5R,6R)-6-[(1S,2E,5R,6S)-2-(cyanomethylidene)-6-hydroxy-5-methoxycyclohex-3-en-1-yl]oxy-3,4,5-tris(2-methylpropanoyloxy)oxan-2-yl]methyl 2-methylpropanoate
• CAS: 352426-53-0
• 化学式: C₃₁H₄₅NO₁₂
• 分子量: 623.698
• InChiKey: BRVJNZUJDORLNM-PCFQWPSTSA-N

物化性质

• 沸点：
  680.9±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (+)-(1E)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以23%的产率得到(-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-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：

  (+)-(1E)-{(4R,5R,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-6-hydroxy-4-methoxycyclohex-2-en-1-yliden}acetonitrile 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 氢氟酸 、 silver trifluoromethanesulfonate 作用下， 以 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 18.0h， 生成 (+)-(1E)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-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