1-[(3aR,4R,6R,6aR)-6-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-trimethylsilyloxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]pyrimidine-2,4-dione | 338780-28-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-[(3aR,4R,6R,6aR)-6-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-trimethylsilyloxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]pyrimidine-2,4-dione
• CAS: 338780-28-2
• 化学式: C₃₃H₃₇N₂O₉PSi
• 分子量: 664.724
• InChiKey: DXJBTJXSKFSWCQ-PTDKRUFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[(3aR,4R,6R,6aR)-6-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-trimethylsilyloxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]pyrimidine-2,4-dione 在 borane diisopropylethylamine complex 作用下， 反应 4.0h， 生成 5'-O-DMT-uridine 2',3'-cyclic boranophosphate
  参考文献：
  名称：

  Synthesis and separation of diastereomers of uridine 2′,3′-cyclic boranophosphate

  摘要：

  The first boron-containing 2',3'-cyclic phosphate-modified analogue, uridine 2',3'-cyclic boranophosphate (2',3'-cyclic-UMPB), was synthesized. 5'-O-Protected uridine was cyclophosphorylated by diphenyl H-phosphonate to yield uridine 2',3'-cyclic H-phosphonate, which upon silylation followed by boronation and subsequent acid treatment gave 2',3'-cyclic-UMPB in high yield. The two diastereomers of 2',3'-cyclic-UMPB were separated by HPLC. An alternative method for synthesis of uridine 2',3'-cyclic phosphorothioate (2',3'-cyclic-UMPS) via H-phosphonate was also described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00700-9
• 作为产物：
  描述：

  5’-O-(4,4’-二甲氧基三苯甲基)尿苷 在 吡啶 、 亚磷酸二苯酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.41h， 生成 1-[(3aR,4R,6R,6aR)-6-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-trimethylsilyloxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and separation of diastereomers of uridine 2′,3′-cyclic boranophosphate

  摘要：

  The first boron-containing 2',3'-cyclic phosphate-modified analogue, uridine 2',3'-cyclic boranophosphate (2',3'-cyclic-UMPB), was synthesized. 5'-O-Protected uridine was cyclophosphorylated by diphenyl H-phosphonate to yield uridine 2',3'-cyclic H-phosphonate, which upon silylation followed by boronation and subsequent acid treatment gave 2',3'-cyclic-UMPB in high yield. The two diastereomers of 2',3'-cyclic-UMPB were separated by HPLC. An alternative method for synthesis of uridine 2',3'-cyclic phosphorothioate (2',3'-cyclic-UMPS) via H-phosphonate was also described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00700-9