2-[2-[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylcarbamoyloxy]ethoxy]ethyl N-[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methyl]carbamate | 669013-02-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 2-[2-[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylcarbamoyloxy]ethoxy]ethyl N-[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methyl]carbamate
• CAS: 669013-02-9
• 化学式: C₄₈H₈₈N₆O₁₅Si₄
• 分子量: 1101.6
• InChiKey: WSDNXYATQUZAQL-BNIJHKBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  73.0
• 可旋转键数：
  32.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  250.99
• 氢给体数：
  4.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2-[2-[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylcarbamoyloxy]ethoxy]ethyl N-[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methyl]carbamate 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 9.0h， 以99%的产率得到2-[2-[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methylcarbamoyloxy]ethoxy]ethyl N-[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl]carbamate
  参考文献：
  名称：

  The First Direct Evaluation of the Two-Active Site Mechanism for Chitin Synthase

  摘要：

  Chitin synthase polymerizes UDP-GlcNAc to form chitin (poly-beta(1,4)-G1cNAc) and is essential for fungal cell wall biosynthesis. The alternating orientation of the GlcNAc residues within the chitin chain has led to the proposal that chitin synthase possesses two active sites. We report the results of the first direct test of this possibility. Two simple uridine-derived dimeric inhibitors are shown to exhibit 10-fold greater inhibition than a monomeric control, consistent with the presence of two active sites. This observation has important implications for the development of antifungal agents, as well as the understanding of polymerizing glycosyltransferases.

  DOI：

  10.1021/jo035100c
• 作为产物：
  描述：

  尿嘧啶核苷 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 三(2-氯乙基)胺 、 氢气 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 33.0h， 生成 2-[2-[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylcarbamoyloxy]ethoxy]ethyl N-[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methyl]carbamate
  参考文献：
  名称：

  The First Direct Evaluation of the Two-Active Site Mechanism for Chitin Synthase

  摘要：

  Chitin synthase polymerizes UDP-GlcNAc to form chitin (poly-beta(1,4)-G1cNAc) and is essential for fungal cell wall biosynthesis. The alternating orientation of the GlcNAc residues within the chitin chain has led to the proposal that chitin synthase possesses two active sites. We report the results of the first direct test of this possibility. Two simple uridine-derived dimeric inhibitors are shown to exhibit 10-fold greater inhibition than a monomeric control, consistent with the presence of two active sites. This observation has important implications for the development of antifungal agents, as well as the understanding of polymerizing glycosyltransferases.

  DOI：

  10.1021/jo035100c