(5aR)-8c-acetoxy-7t-acetoxymethyl-3-methyl-(5ar,8ac)-5a,7,8,8a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a][1,3,5]triazine-2,4-dione | 66528-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: (5aR)-8c-acetoxy-7t-acetoxymethyl-3-methyl-(5ar,8ac)-5a,7,8,8a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a][1,3,5]triazine-2,4-dione
• 英文别名: O^{3'_,O5'_{-diacetyl-3-methyl-arabino-5-aza-6,O}2'}-cyclo-uridine；[(2R,4R,5R,6S)-5-acetyloxy-11-methyl-10,12-dioxo-3,7-dioxa-1,9,11-triazatricyclo[6.4.0.02,6]dodec-8-en-4-yl]methyl acetate
• CAS: 66528-43-6
• 化学式: C₁₃H₁₅N₃O₈
• 分子量: 341.277
• InChiKey: PWWGCSSBYJIISC-DOLQZWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-amino-3',5'-bis(O-t-butyldimethylsilyl)-β-D-arabinofurano<1',2':4,5>-2-oxazoline 生成 (5aR)-8c-acetoxy-7t-acetoxymethyl-3-methyl-(5ar,8ac)-5a,7,8,8a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a][1,3,5]triazine-2,4-dione
  参考文献：
  名称：

  .beta.-D-Arabinofuran[1',2':4,5]oxazolo-1,3,5-triazine-5-N-methyl-4,6-dione and analogs, unusually specific immunosuppressive agents

  摘要：

  Sequential treatment of the protected beta-D-arabinofuran[1',2':4,5]-2-aminooxazoline (2) with methyl isocyanate and diimidazole carbonyl afforded the 2,2'-anhydro-beta-D-arabinofuranosyl nucleoside, 6. Deprotection and hydrolysis yielded the corresponding arabinoside. Although the anhydronucleoside exhibited in vitro antiviral activity against herpes simplex type 1, it exacerbated the infection in vivo. Further examination uncovered an in vitro inhibition of the induction of a cell-mediated immune response without cytotoxicity.

  DOI：

  10.1021/jm00204a011

文献信息

• .beta.-D-Arabinofuran[1',2':4,5]oxazolo-1,3,5-triazine-5-N-methyl-4,6-dione and analogs, unusually specific immunosuppressive agents
  作者：W. Wierenga、B. E. Loughman、A. J. Gibbons、H. E. Renis

  DOI：10.1021/jm00204a011

  日期：1978.6

  Sequential treatment of the protected beta-D-arabinofuran[1',2':4,5]-2-aminooxazoline (2) with methyl isocyanate and diimidazole carbonyl afforded the 2,2'-anhydro-beta-D-arabinofuranosyl nucleoside, 6. Deprotection and hydrolysis yielded the corresponding arabinoside. Although the anhydronucleoside exhibited in vitro antiviral activity against herpes simplex type 1, it exacerbated the infection in vivo. Further examination uncovered an in vitro inhibition of the induction of a cell-mediated immune response without cytotoxicity.