2,3,4-tri-O-acetyl-6-O-2-nitrobenzyl-α-D-galactopyranosyl hydrogenphosphonate triethylammonium salt | 1023293-30-2

• 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-tri-O-acetyl-6-O-2-nitrobenzyl-α-D-galactopyranosyl hydrogenphosphonate triethylammonium salt
• CAS: 1023293-30-2
• 化学式: C₆H₁₅N*C₁₉H₂₄NO₁₃P
• 分子量: 606.564
• InChiKey: AHOMDILVLPFFPM-DMFXPACMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  190.27
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-O-2-nitrobenzyl-α-D-galactopyranosyl hydrogenphosphonate triethylammonium salt 、 9-芴甲醇 在 吡啶 、 三甲基乙酰氯 、 碘 作用下， 以 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis and photolytic activation of 6″-O-2-nitrobenzyl uridine-5′-diphosphogalactose: a ‘caged’ UDP-Gal derivative

  摘要：

  Placing an 2-nitrobenzyl group on O-6 of the galactosyl residue in uridine-5'-diphosphogalactose (UDP-Gal) gives 6 ''-O-2-nitrobenzyl-UDP-Gal that is shown to be inactive as a donor substrate for beta-(1 -> 4)-galactosyltransferase (GalT). On irradiation at 365 nm, the nitrobenzyl group is completely removed yielding native UDP-Gal that then transfers normally to produce the expected beta Gal-(1 -> 4)-beta GlcNAc disaccharidic linkage. 6 ''-O-2-Nitrobenzyl-UDP-Gal thus fulfils the minimum requirements of a 'caged' UDP-Gal for application in time-resolved crystallographic studies of beta-(1 -> 4)-GalT. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.01.021
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-O-2-nitrobenzyl-D-galactopyranose 、 三乙胺 在 咪唑 、 三氯化磷 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以62%的产率得到2,3,4-tri-O-acetyl-6-O-2-nitrobenzyl-α-D-galactopyranosyl hydrogenphosphonate triethylammonium salt
  参考文献：
  名称：

  Synthesis and photolytic activation of 6″-O-2-nitrobenzyl uridine-5′-diphosphogalactose: a ‘caged’ UDP-Gal derivative

  摘要：

  Placing an 2-nitrobenzyl group on O-6 of the galactosyl residue in uridine-5'-diphosphogalactose (UDP-Gal) gives 6 ''-O-2-nitrobenzyl-UDP-Gal that is shown to be inactive as a donor substrate for beta-(1 -> 4)-galactosyltransferase (GalT). On irradiation at 365 nm, the nitrobenzyl group is completely removed yielding native UDP-Gal that then transfers normally to produce the expected beta Gal-(1 -> 4)-beta GlcNAc disaccharidic linkage. 6 ''-O-2-Nitrobenzyl-UDP-Gal thus fulfils the minimum requirements of a 'caged' UDP-Gal for application in time-resolved crystallographic studies of beta-(1 -> 4)-GalT. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.01.021