1,6-di-O-acetyl-2,3,4-tri-O-benzyl-5a-difluoro-5a-carba-α-D-galactopyranose | 949886-90-2

• 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: 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-5a-difluoro-5a-carba-α-D-galactopyranose
• 英文别名: [(1R,3R,4R,5S,6S)-3-acetyloxy-2,2-difluoro-4,5,6-tris(phenylmethoxy)cyclohexyl]methyl acetate
• CAS: 949886-90-2
• 化学式: C₃₂H₃₄F₂O₇
• 分子量: 568.615
• InChiKey: XVMUYGZWMAWFSQ-GGEKVXJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,6-di-O-acetyl-2,3,4-tri-O-benzyl-5a-difluoro-5a-carba-α-D-galactopyranose 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、202.66 kPa 条件下， 反应 9.0h， 生成 gem-difluorocarba-α-D-galactopyranose
  参考文献：
  名称：

  gem-Difluoro-carbasugars, the cases of mannopyranose and galactopyranose

  摘要：

  5a-Difluoro-5a-carbamannopyranose (gem-difluoro-carbamannopyranose) and 5a-difluoro-5a-carbagalactopyranose (gem-di-difluoro-carbagalactopyranose), close congeners of their respective natural sugars, in which the endocyclic oxygen atom has been replaced by a gem-difluoromethylene group, were synthesized from D-mannose and D-galactose, using a rearrangement strategy. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.05.021
• 作为产物：
  描述：

  、 乙酸酐 以 吡啶 为溶剂， 以32.4 mg的产率得到1,6-di-O-acetyl-2,3,4-tri-O-benzyl-5a-difluoro-5a-carba-α-D-galactopyranose
  参考文献：
  名称：

  gem-Difluoro-carbasugars, the cases of mannopyranose and galactopyranose

  摘要：

  5a-Difluoro-5a-carbamannopyranose (gem-difluoro-carbamannopyranose) and 5a-difluoro-5a-carbagalactopyranose (gem-di-difluoro-carbagalactopyranose), close congeners of their respective natural sugars, in which the endocyclic oxygen atom has been replaced by a gem-difluoromethylene group, were synthesized from D-mannose and D-galactose, using a rearrangement strategy. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.05.021

文献信息

• First synthesis of 5-fluoro-(+)-MK7607, its 1-epimer and 6-deoxy derivative
  作者：João Sardinha、Amelia Pilar Rauter、Matthieu Sollogoub

  DOI：10.1016/j.tetlet.2008.07.070

  日期：2008.9

  (+)-MK7607 is a patented naturally occurring unsaturated pseudo-carbasugar possessing herbicidal activity. We present herein the first synthesis of the 5-fluorinated analogue (1S, 2S, 3R, 4R)-5-fluoro-6-(hydroxymethyl)cyclohex-5-ene-1,2,3,4-tetrol as well as that of two related compounds, namely its 1-epimer and its 6-deoxy derivative. (C) 2008 Elsevier Ltd. All rights reserved.

  (+)-MK7607 是一种具有除草活性的专利天然不饱和伪类碳水化合物。本文首次报道了5-氟化类似物（1S,2S,3R,4R）-5-氟-6-(羟甲基)环己-5-烯-1,2,3,4-四醇及其两种相关化合物（即其1-异构体和6-去氧衍生物）的合成。 (C) 2008 《欧洲化学期刊》所有权利保留。