(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucpyranosyl) dibenzyl phosphate | 884856-12-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucpyranosyl) dibenzyl phosphate
• CAS: 884856-12-6
• 化学式: C₄₁H₄₂N₃O₈P
• 分子量: 735.774
• InChiKey: SZPIGHUOUCEKFN-JYSLIDIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.34
• 重原子数：
  53.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  130.44
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucpyranosyl) dibenzyl phosphate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 20.0 ℃ 、6.5 MPa 条件下， 反应 72.0h， 以67%的产率得到D-氨基葡萄糖-1-磷酸
  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：

  二苯基N,N'-二异丙基亚磷酰胺 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucpyranosyl) dibenzyl 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