Acetic acid (2S,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester | 188913-43-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2S,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2S,3S,4R,5S,6R)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 188913-43-1
• 化学式: C₁₆H₂₀Cl₃NO₁₀
• 分子量: 492.695
• InChiKey: IBUZGVQIKARDAF-PDWCTOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  147.51
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S)-2-β-L-glucopyranosyloxy-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  Diastereoselective synthesis of the benzoxazinone acetal glucoside ent-GDIMBOA: the first enantiomer of a natural acetal glucoside

  摘要：

  The synthesis of (2S)-2-beta-L-glucopyranosyloxy-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, the enantiomer of the natural acetal glucoside GDIMBOA from maize, has been achieved by the double diastereoselective L-glucosylation of racemic 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one with 2,3,4,6-tetra-O-acetyl-beta-L-glucopyranosyl trichloroacetimidate in the presence of excess of boron trifluoride etherate as promoter as well as protecting and equilibrating agent. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00303-5
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide 在 potassium carbonate 、 silver carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.5h， 生成 Acetic acid (2S,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Diastereoselective synthesis of the benzoxazinone acetal glucoside ent-GDIMBOA: the first enantiomer of a natural acetal glucoside

  摘要：

  The synthesis of (2S)-2-beta-L-glucopyranosyloxy-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, the enantiomer of the natural acetal glucoside GDIMBOA from maize, has been achieved by the double diastereoselective L-glucosylation of racemic 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one with 2,3,4,6-tetra-O-acetyl-beta-L-glucopyranosyl trichloroacetimidate in the presence of excess of boron trifluoride etherate as promoter as well as protecting and equilibrating agent. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00303-5