methyl 2,3,4-tri-O-benzyl-6-deoxy-6,6-difluoro-α-D-glucopyranoside | 146197-18-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-deoxy-6,6-difluoro-α-D-glucopyranoside
• 英文别名: (2S,3S,4S,5R,6S)-2-(difluoromethyl)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 146197-18-4
• 化学式: C₂₈H₃₀F₂O₅
• 分子量: 484.54
• InChiKey: MAWROVSABOKRSC-SVNGMSFNSA-N

物化性质

• 沸点：
  564.4±50.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6,6-difluoro-α-D-glucopyranoside 在 盐酸 、 氯化亚砜 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.25h， 生成 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis and evaluation of new 6-deoxy-6-fluorinated glucosides as inhibitors of yeast α-glucosidase

  摘要：

  A series of 6-deoxy-6-fluorinated glucosides have been synthesized and evaluated as inhibitors of yeast alpha-glucosidase. These compounds have a 7- to 25-fold higher affinity than.the corresponding 6-hydroxy derivatives. The most potent inhibitor in the series was the new compound 6-deoxy-6-fluoro-(3-trimethylsilyl)propyl-alpha-D-glucopyranoside (3e) prepared by condensing 2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-alpha-D-glucosylchloride with 3-trimethylsilylpropanol.

  DOI：

  10.1016/s0022-1139(00)82408-2
• 作为产物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 在 二乙胺基三氟化硫 、 二甲基亚砜 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-deoxy-6,6-difluoro-α-D-glucopyranoside
  参考文献：
  名称：

  An Efficient Synthesis of the Glycosidase Inhibitor 1,6-Dideoxy-6,6-difluoronojirimycin

  摘要：

  1,6-二去氧-6,6-二氟诺吉林霉素（1）是从易得且商业可获得的起始物质，甲基2,3,4-三O-苄基-α-D-葡萄糖吡喃糖苷制备而成。该合成的关键步骤是使用DAST进行二氟化反应和还原胺化反应。合成的总产率为44%。化合物1已经被测试其作为各种葡萄糖苷酶和半乳糖苷酶的抑制剂的活性。

  DOI：

  10.1515/znb-2011-0809

文献信息

• CDP-6-deoxy-6,6-difluoro-<scp>d</scp>-glucose:  A Mechanism-Based Inhibitor for CDP-<scp>d</scp>-glucose 4,6-Dehydratase
  作者：Cheng-Wei T. Chang、Xuemei H. Chen、Hung-wen Liu

  DOI：10.1021/ja982198h

  日期：1998.9.1
• Synthesis of 6-deoxy-6,6-difluoro-α-d-glucopyranosyl fluoride
  作者：Lincoln A. Noecker、John R. Edwards

  DOI：10.1016/s0040-4039(97)01317-8

  日期：1997.8

  The synthesis of 6-deoxy-6,6-difluora-alpha-D-glucopyranosyl fluoride from the benzyl-protected methylglucoside was accomplished in six steps. (C) 1997 Elsevier Science Ltd.
• Synthesis and evaluation of new 6-deoxy-6-fluorinated glucosides as inhibitors of yeast α-glucosidase
  作者：Serge Halazy、Véronique Berges、Anne Ehrhard、Charles Danzin

  DOI：10.1016/s0022-1139(00)82408-2

  日期：1992.11

  A series of 6-deoxy-6-fluorinated glucosides have been synthesized and evaluated as inhibitors of yeast alpha-glucosidase. These compounds have a 7- to 25-fold higher affinity than.the corresponding 6-hydroxy derivatives. The most potent inhibitor in the series was the new compound 6-deoxy-6-fluoro-(3-trimethylsilyl)propyl-alpha-D-glucopyranoside (3e) prepared by condensing 2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-alpha-D-glucosylchloride with 3-trimethylsilylpropanol.
• An Efficient Synthesis of the Glycosidase Inhibitor 1,6-Dideoxy-6,6-difluoronojirimycin
  作者：René Csuk、Erik Prell、Claudia Korb

  DOI：10.1515/znb-2011-0809

  日期：2011.8.1

  1,6-Dideoxy-6,6-difluoronojirimycin (1) was prepared from an easily accessible and commercially available starting material, methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside. Key steps of this synthesis are a difluorination reaction using DAST and a reductive amination. The overall yield of the synthesis is 44%. Compound 1 has been tested for its activity as an inhibitor of various glucosidases and galactosidases.

  1,6-二去氧-6,6-二氟诺吉林霉素（1）是从易得且商业可获得的起始物质，甲基2,3,4-三O-苄基-α-D-葡萄糖吡喃糖苷制备而成。该合成的关键步骤是使用DAST进行二氟化反应和还原胺化反应。合成的总产率为44%。化合物1已经被测试其作为各种葡萄糖苷酶和半乳糖苷酶的抑制剂的活性。