(2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol | 596834-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol
• 英文别名: [(2S,3S,4aS,5S,8R,8aR)-6-bromo-2,3-dimethoxy-2,3-dimethyl-8-phenylmethoxy-4a,5,8,8a-tetrahydro-1,4-benzodioxin-5-yl] acetate
• CAS: 596834-82-1
• 化学式: C₂₁H₂₇BrO₇
• 分子量: 471.345
• InChiKey: VLFQHKOODQUUBT-SOXBMFEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol 在 草酰氯 、 potassium carbonate 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (2'S,3'S,4R,5R,6S)-2-bromo-4-O-benzyl-5-O,6-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohex-2-en-1-one-3,4,5-triol
  参考文献：
  名称：

  Difluorinated analogues of shikimic acid

  摘要：

  Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00697-5
• 作为产物：
  描述：

  乙酸酐 、 (2'S,3'S,3R,4R,5S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohex-1-ene-3,4,5,6-tetraol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol
  参考文献：
  名称：

  Difluorinated analogues of shikimic acid

  摘要：

  Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00697-5