(2'S,3'S,3R,4R,5S)-1-methoxycarbonyl-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6,6-difluoro-cyclohex-1-ene-3,4,5-triol | 701211-79-2

• 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)-1-methoxycarbonyl-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6,6-difluoro-cyclohex-1-ene-3,4,5-triol
• 英文别名: methyl (2S,3S,4aS,8R,8aR)-5,5-difluoro-2,3-dimethoxy-2,3-dimethyl-8-phenylmethoxy-8,8a-dihydro-4aH-1,4-benzodioxine-6-carboxylate
• CAS: 701211-79-2
• 化学式: C₂₁H₂₆F₂O₇
• 分子量: 428.43
• InChiKey: XNXFOHBHWOPMLD-JOMPHRNESA-N

物化性质

• 熔点：
  131-133 °C
• 沸点：
  462.9±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 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：
  9

反应信息

• 作为反应物：
  描述：

  (2'S,3'S,3R,4R,5S)-1-methoxycarbonyl-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6,6-difluoro-cyclohex-1-ene-3,4,5-triol 在 水 、 三氟乙酸 作用下， 反应 3.0h， 以100%的产率得到(3R,4S,5S)-1-methoxycarbonyl-3-O-benzyl-6,6-difluoro-cyclohex-1-ene-3,4,5-triol
  参考文献：
  名称：

  Arene cis-dihydrodiols—useful precursors for the preparation of antimetabolites of the shikimic acid pathway: application to the synthesis of 6,6-difluoroshikimic acid and (6S)-6-fluoroshikimic acid

  摘要：

  The synthesis of 6,6-difluoroshikimic acid (11) has been achieved in ten steps from the enantiopure diol 16, which is derived from enzymatic cis-dihydroxylation of iodobenzene. The versatility of the synthetic strategy has been demonstrated by the preparation of the known antimicrobial agent, (6S)-6-fluoroshikimic acid (5). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.029
• 作为产物：
  描述：

  (2'S,3'S,3R,4R,5R,6S)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-cyclohex-1-ene-3,4,5,6-tetraol 在 三(2-呋喃基)膦 、 palladium diacetate 草酰氯 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 (2'S,3'S,3R,4R,5S)-1-methoxycarbonyl-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6,6-difluoro-cyclohex-1-ene-3,4,5-triol
  参考文献：
  名称：

  Arene cis-dihydrodiols—useful precursors for the preparation of antimetabolites of the shikimic acid pathway: application to the synthesis of 6,6-difluoroshikimic acid and (6S)-6-fluoroshikimic acid

  摘要：

  The synthesis of 6,6-difluoroshikimic acid (11) has been achieved in ten steps from the enantiopure diol 16, which is derived from enzymatic cis-dihydroxylation of iodobenzene. The versatility of the synthetic strategy has been demonstrated by the preparation of the known antimicrobial agent, (6S)-6-fluoroshikimic acid (5). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.029

文献信息

• The synthesis of 6,6-difluoroshikimic acid
  作者：Jane L. Humphreys、David J. Lowes、Karen A. Wesson、Roger C. Whitehead

  DOI：10.1016/j.tetlet.2004.03.033

  日期：2004.4

  The synthesis of 6.6-difluoroshikimic acid (4) has been achieved in nine Steps from the enantiopure diol 9, which is derived from microbial dihydroxylation of iodobenzene. The synthetic strategy has also been demonstrated to be applicable to the preparation of other 6-substituted anologues of shikimic acid. (C) 2004 Elsevier Ltd. All rights reserved.
• Arene cis-dihydrodiols—useful precursors for the preparation of antimetabolites of the shikimic acid pathway: application to the synthesis of 6,6-difluoroshikimic acid and (6S)-6-fluoroshikimic acid
  作者：Jane L. Humphreys、David J. Lowes、Karen A. Wesson、Roger C. Whitehead

  DOI：10.1016/j.tet.2006.03.029

  日期：2006.5

  The synthesis of 6,6-difluoroshikimic acid (11) has been achieved in ten steps from the enantiopure diol 16, which is derived from enzymatic cis-dihydroxylation of iodobenzene. The versatility of the synthetic strategy has been demonstrated by the preparation of the known antimicrobial agent, (6S)-6-fluoroshikimic acid (5). (c) 2006 Elsevier Ltd. All rights reserved.