[(2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl 2-fluoro-3,5-dinitrobenzoate | 330184-00-4

• 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: [(2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl 2-fluoro-3,5-dinitrobenzoate
• CAS: 330184-00-4
• 化学式: C₂₈H₂₇FN₂O₁₁
• 分子量: 586.528
• InChiKey: LXVFHQCYIOKJAL-YKUHLWEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  175
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-mannopyranose 、 [(2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl 2-fluoro-3,5-dinitrobenzoate 在 4-二甲氨基吡啶 、 lithium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以53%的产率得到[(2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl 3,5-dinitro-2-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxybenzoate
  参考文献：
  名称：

  Intramolecular Glycosylation under Neutral Conditions for Synthesis of 1,4-Linked Disaccharides

  摘要：

  [GRAPHICS]A new method for intramolecular glycosylation, in which the donor and acceptor were linked via a 3,4-dinitrosalicylic acid derivative, was developed. Simply dissolving the tethered glycoside in CH3NO2 and warming to 40-60 degreesC led to formation of 1,4-linked disaccharides under neutral, hence, exceptionally mild, conditions.

  DOI：

  10.1021/ol006988j
• 作为产物：
  描述：

  2-氟-3,5-二硝基苯甲酸 、 2,3-二-o-苄基-alpha-d-吡喃葡萄糖苷甲酯 在 草酰氯 、 2,6-二甲基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 以63%的产率得到[(2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl 2-fluoro-3,5-dinitrobenzoate
  参考文献：
  名称：

  Intramolecular Glycosylation under Neutral Conditions for Synthesis of 1,4-Linked Disaccharides

  摘要：

  [GRAPHICS]A new method for intramolecular glycosylation, in which the donor and acceptor were linked via a 3,4-dinitrosalicylic acid derivative, was developed. Simply dissolving the tethered glycoside in CH3NO2 and warming to 40-60 degreesC led to formation of 1,4-linked disaccharides under neutral, hence, exceptionally mild, conditions.

  DOI：

  10.1021/ol006988j

文献信息

• Intramolecular Glycosylation under Neutral Conditions for Synthesis of 1,4-Linked Disaccharides
  作者：Jane B. Laursen、Lars Petersen、Knud J. Jensen

  DOI：10.1021/ol006988j

  日期：2001.3.1

  [GRAPHICS]A new method for intramolecular glycosylation, in which the donor and acceptor were linked via a 3,4-dinitrosalicylic acid derivative, was developed. Simply dissolving the tethered glycoside in CH3NO2 and warming to 40-60 degreesC led to formation of 1,4-linked disaccharides under neutral, hence, exceptionally mild, conditions.