succinic acid mono-3-N-benzoyl-2',3'-O-isopropylidene-uridin-5'-yl ester | 1173990-81-2

• 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: succinic acid mono-3-N-benzoyl-2',3'-O-isopropylidene-uridin-5'-yl ester
• CAS: 1173990-81-2
• 化学式: C₂₃H₂₄N₂O₁₀
• 分子量: 488.451
• InChiKey: DKVZAYIJCITCAN-AZVUBCEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  152.36
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (5-amino-2-pyridyl) 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 、 succinic acid mono-3-N-benzoyl-2',3'-O-isopropylidene-uridin-5'-yl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 反应 17.0h， 以23%的产率得到[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-oxo-4-[[6-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpyridin-3-yl]amino]butanoate
  参考文献：
  名称：

  5-Amino-2-pyridyl 1-thioglycosides in synthesis of analogs of glycosyltransferases substrates

  摘要：

  We present the synthesis of 1-thioglycosyl derivatives of uridine. which were designed to act as potential donor substrates for glycosyltransferases. We constructed such analogs using 5-amino-2-pyridyl 1-thioglycosides as glycosyl units which were connected to uridine via succinic linker. For preparation of the amide bonds we applied different condensation procedures. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2009.04.002
• 作为产物：
  描述：

  丁二酸酐 、 N³-benzoyl-2',3'-O-isopropylidene uridine 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以48%的产率得到succinic acid mono-3-N-benzoyl-2',3'-O-isopropylidene-uridin-5'-yl ester
  参考文献：
  名称：

  5-Amino-2-pyridyl 1-thioglycosides in synthesis of analogs of glycosyltransferases substrates

  摘要：

  We present the synthesis of 1-thioglycosyl derivatives of uridine. which were designed to act as potential donor substrates for glycosyltransferases. We constructed such analogs using 5-amino-2-pyridyl 1-thioglycosides as glycosyl units which were connected to uridine via succinic linker. For preparation of the amide bonds we applied different condensation procedures. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2009.04.002