2-deoxy-2-isobutyramido-α-D-glucopyranosyl phosphate | 884856-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-isobutyramido-α-D-glucopyranosyl phosphate
• 英文别名: [(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(2-methylpropanoylamino)oxan-2-yl] dihydrogen phosphate
• CAS: 884856-19-3
• 化学式: C₁₀H₂₀NO₉P
• 分子量: 329.244
• InChiKey: BCZDIRVBOQDJEE-VRRGKTLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-isobutyramido-α-D-glucopyranosyl phosphate 、 N,N'-二环己基-4-吗啉甲脒-5'-O-[羟基(4-吗啉基)磷酰]尿苷(1:1) 在 Dowex 50-X₈ triethylammonium form 作用下， 以 水 、 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以30%的产率得到uridine-5'-(2-isobutyramido-2-deoxy-α-D-glucopyranosyl diphosphate)
  参考文献：
  名称：

  Artificial N-functionalized UDP-glucosamine analogues as modified substrates for N-acetylglucosaminyl transferases

  摘要：

  Analogues of UDP-GlcNAc modified at the 2-acetamido group of the GlcNAc moiety were prepared in order to study their role in the mechanism of N-acetylglucosaminyl transferase mediated glycosylation reactions. The structural analogues with N-formyl-, N-propionyl-, N-butyryl- and N-isobutyryl-groups were synthesized, utilizing the morpholidate coupling method starting from D-glucosaminyl-1-phosphate after selective N-acylation of its amino group with the appropriate N-acyloxysuccinimide esters as well as a chlorinated formylformiate. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.017
• 作为产物：
  描述：

  2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 在 palladium on activated charcoal 四氮唑 、 氢氧化钾 、 氢气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、6.5 MPa 条件下， 反应 77.0h， 生成 2-deoxy-2-isobutyramido-α-D-glucopyranosyl phosphate
  参考文献：
  名称：

  Artificial N-functionalized UDP-glucosamine analogues as modified substrates for N-acetylglucosaminyl transferases

  摘要：

  Analogues of UDP-GlcNAc modified at the 2-acetamido group of the GlcNAc moiety were prepared in order to study their role in the mechanism of N-acetylglucosaminyl transferase mediated glycosylation reactions. The structural analogues with N-formyl-, N-propionyl-, N-butyryl- and N-isobutyryl-groups were synthesized, utilizing the morpholidate coupling method starting from D-glucosaminyl-1-phosphate after selective N-acylation of its amino group with the appropriate N-acyloxysuccinimide esters as well as a chlorinated formylformiate. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.017

文献信息

• Artificial N-functionalized UDP-glucosamine analogues as modified substrates for N-acetylglucosaminyl transferases
  作者：Daniel Lazarević、Joachim Thiem

  DOI：10.1016/j.carres.2006.01.017

  日期：2006.4

  Analogues of UDP-GlcNAc modified at the 2-acetamido group of the GlcNAc moiety were prepared in order to study their role in the mechanism of N-acetylglucosaminyl transferase mediated glycosylation reactions. The structural analogues with N-formyl-, N-propionyl-, N-butyryl- and N-isobutyryl-groups were synthesized, utilizing the morpholidate coupling method starting from D-glucosaminyl-1-phosphate after selective N-acylation of its amino group with the appropriate N-acyloxysuccinimide esters as well as a chlorinated formylformiate. (c) 2006 Elsevier Ltd. All rights reserved.