(2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-6-(2,4-二硝基苯氧基)-5-氟-4-羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇 | 154862-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-6-(2,4-二硝基苯氧基)-5-氟-4-羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
• 中文别名: 2',4'-二硝基苯基-2-脱氧-2-氟纤维二糖糖苷
• 英文名称: 2,4-dinitrophenyl 2-deoxy-2-fluoro-β-cellobioside
• 英文别名: (2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-6-(2,4-dinitrophenoxy)-5-fluoro-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 154862-23-4
• 化学式: C₁₈H₂₃FN₂O₁₄
• 分子量: 510.384
• InChiKey: WFVCNOHOODVBQK-IUBYCILNSA-N

物化性质

• 沸点：
  822.4±65.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  250
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  2,4-dinitrophenyl 3,6,2',3',4',6'-hexa-O-acetyl-2-deoxy-2-fluoro-β-cellobioside 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以35%的产率得到(2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-6-(2,4-二硝基苯氧基)-5-氟-4-羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
  参考文献：
  名称：

  Syntheses of 2-deoxy-2-fluoro mono- and oligo-saccharide glycosides from glycals and evaluation as glycosidase inhibitors

  摘要：

  Several fluorinated oligosaccharides, including 2-deoxy-2-fluoro derivatives of cellobiose, maltose, and maltotriose were synthesized by the action of fluorine or acetyl hypofluorite on the corresponding glycal peracetates. Temperature effects on the stereoselectivities of these reactions were examined. Addition of acetyl hypofluorite to several 2-substituted glycals in the gluco or galacto series gave 2,2-disubstituted arabino- or lyxo-hexose derivatives; 3,4,6-tri-O-acetyl-2-fluoro-D-glucal or the analogous galactal yielded 2-deoxy-2,2-difluoro arabino- or lyxo-hexose peracetates, whereas 2-acetoxy-3,4,6-tri-O-acetyl-D-glucal or the analogous galactal gave 2(R)-2-acetoxy-2-fluoro-arabino- or lyxo-hexose peracetates, respectively. 2-Acetamido-3,4,6-tri-O-acetyl-D-glucal gave 2(R)-2-acetamido-2-acetoxy-3,4,6-tri-O-acetyl-alpha-D-arabino-hexopyranosyl fluoride. 2,4-Dinitrophenyl 2-deoxy-2-fluoro-beta-cellobioside was an inactivator of the exoglucanase from Cellulomonas fimi while 2-deoxy-2-fluoro-alpha-maltosyl and alpha-maltotriosyl fluorides were slow substrates of human pancreatic alpha-amylase and rabbit muscle glycogen debranching enzyme, respectively.

  DOI：

  10.1016/0008-6215(93)84061-a

文献信息

• Glycosynthases:  Mutant Glycosidases for Oligosaccharide Synthesis
  作者：Lloyd F. Mackenzie、Qingping Wang、R. Antony J. Warren、Stephen G. Withers

  DOI：10.1021/ja980833d

  日期：1998.6.1
• US6716421B2
  申请人：——

  公开号：US6716421B2

  公开（公告）日：2004-04-06
• US6969512B2
  申请人：——

  公开号：US6969512B2

  公开（公告）日：2005-11-29
• US6964124B2
  申请人：——

  公开号：US6964124B2

  公开（公告）日：2005-11-15
• US7030156B2
  申请人：——

  公开号：US7030156B2

  公开（公告）日：2006-04-18