2,3,4-tri-O-acetyl-6-O-trityl-D-glucopyranosyl (N-phenyl)trifluoroacetimidate | 590368-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,3,4-tri-O-acetyl-6-O-trityl-D-glucopyranosyl (N-phenyl)trifluoroacetimidate
• 英文别名: [(2R,3R,4S,5R)-4,5-diacetyloxy-6-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxy-2-(trityloxymethyl)oxan-3-yl] acetate
• CAS: 590368-05-1
• 化学式: C₃₉H₃₆F₃NO₉
• 分子量: 719.711
• InChiKey: LVILCVXGUBPJAO-KXCACMGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  决明内酯 、 2,3,4-tri-O-acetyl-6-O-trityl-D-glucopyranosyl (N-phenyl)trifluoroacetimidate 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 氯苯 为溶剂， 反应 15.0h， 以24%的产率得到[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-(10-hydroxy-7-methoxy-3-methyl-1-oxobenzo[g]isochromen-9-yl)oxy-2-(trityloxymethyl)oxan-3-yl] acetate
  参考文献：
  名称：

  Total Synthesis of the Antiallergic Naphtho-α-pyrone Tetraglucoside, Cassiaside C₂, Isolated from Cassia Seeds

  摘要：

  Toralactone 9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1, cassiaside C-2) isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-alpha-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.

  DOI：

  10.1021/jo034223u
• 作为产物：
  描述：

  6-O-（三苯甲基）-D-吡喃葡萄糖四乙酸酯 在 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 生成 2,3,4-tri-O-acetyl-6-O-trityl-D-glucopyranosyl (N-phenyl)trifluoroacetimidate
  参考文献：
  名称：

  Total Synthesis of the Antiallergic Naphtho-α-pyrone Tetraglucoside, Cassiaside C₂, Isolated from Cassia Seeds

  摘要：

  Toralactone 9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1, cassiaside C-2) isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-alpha-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.

  DOI：

  10.1021/jo034223u