2,3,4,6-tetra-O-isobutyryl-α-D-mannopyranosyl fluoride | 243120-92-5

• 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: 2,3,4,6-tetra-O-isobutyryl-α-D-mannopyranosyl fluoride
• CAS: 243120-92-5
• 化学式: C₂₂H₃₅FO₉
• 分子量: 462.513
• InChiKey: KNZFQOLVTBJXLE-ZBRFXRBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,6-bis[3-(3-carboxymethylphenyl)-4-hydroxyphenyl]hexane 、 2,3,4,6-tetra-O-isobutyryl-α-D-mannopyranosyl fluoride 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium methylate 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 7.0h， 生成 比莫西糖 、 [5'-{6-[3'-Carboxymethyl-6-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-biphenyl-3-yl]-hexyl}-2'-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-biphenyl-3-yl]-acetic acid 、 2-[3-[5-[6-[4-[[(3aS,5R,6S,7S,7aS)-6,7-dihydroxy-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-2-yl]oxy]-3-[3-(carboxymethyl)phenyl]phenyl]hexyl]-2-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenyl]acetic acid
  参考文献：
  名称：

  Stereospecific α-d-mannosylation

  摘要：

  The stereospecific formation of alpha-D-mannosyl glycosidic linkages has been achieved in high yield using tetra-O-pivaloyl-alpha-D-mannopyranosyl fluoride and boron trifluoride diethyl etherate in dichloromethane. Examples of the alpha-D-mannosylation of primary, secondary, benzylic and phenolic hydroxyl groups are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00065-8
• 作为产物：
  描述：

  2,3,4,6-四邻乙酰基-alpha-d-吡喃甘露糖氟化物 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 2,3,4,6-tetra-O-isobutyryl-α-D-mannopyranosyl fluoride
  参考文献：
  名称：

  Stereospecific α-d-mannosylation

  摘要：

  The stereospecific formation of alpha-D-mannosyl glycosidic linkages has been achieved in high yield using tetra-O-pivaloyl-alpha-D-mannopyranosyl fluoride and boron trifluoride diethyl etherate in dichloromethane. Examples of the alpha-D-mannosylation of primary, secondary, benzylic and phenolic hydroxyl groups are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00065-8