(3''-R)-1-[2',5'-bis(O-tert-butyldimethylsilyl)-3'-deoxy-β-D-xylofuranosyl]uracil-3'-spiro-2''-(3''-methoxycarbonyloxirane) | 272780-78-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3''-R)-1-[2',5'-bis(O-tert-butyldimethylsilyl)-3'-deoxy-β-D-xylofuranosyl]uracil-3'-spiro-2''-(3''-methoxycarbonyloxirane)
• 英文别名: methyl (1R,3R,4R,6R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(2,4-dioxopyrimidin-1-yl)-2,5-dioxaspiro[2.4]heptane-1-carboxylate；methyl (2R,3R,4R,5R,7R)-4-[tert-butyl(dimethyl)silyl]oxy-7-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)-1,6-dioxaspiro[2.4]heptane-2-carboxylate
• CAS: 272780-78-6
• 化学式: C₂₄H₄₂N₂O₈Si₂
• 分子量: 542.777
• InChiKey: DIOPLPHLHKNLDY-QFFCLMPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3''-R)-1-[2',5'-bis(O-tert-butyldimethylsilyl)-3'-deoxy-β-D-xylofuranosyl]uracil-3'-spiro-2''-(3''-methoxycarbonyloxirane) 在 一水合肼 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.33h， 生成 1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(ethoxycarbonylmethyl)-β-D-xylo-pentofuranosyl]uracil
  参考文献：
  名称：

  Highly Stereoselective Synthesis and Biological Properties of Nucleoside Analogues Bearing a Spiro Inserted Oxirane Ring

  摘要：

  Starting from 2',5'-di-O-TBDMS-3'-ketouridine 1 or its thymine analogue 2, both xylo (3-10) and ribo (20) epimers of a series of 3"-substituted 3'-spironucleosides have been obtained in good yields and with a total stereoselectivity. Most new compounds were moderately cytotoxic with in some cases slightly selective antiproliferative activities. None of these compounds was active against HIV, but some other antiviral activities against HSV-2, CMV, EBV, or VZV, in the micromolar range, were noted in specific cases.

  DOI：

  10.1080/15257770008035024
• 作为产物：
  描述：

  2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine 、 溴乙酸甲酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以78%的产率得到(3''-R)-1-[2',5'-bis(O-tert-butyldimethylsilyl)-3'-deoxy-β-D-xylofuranosyl]uracil-3'-spiro-2''-(3''-methoxycarbonyloxirane)
  参考文献：
  名称：

  Highly Stereoselective Synthesis and Biological Properties of Nucleoside Analogues Bearing a Spiro Inserted Oxirane Ring

  摘要：

  Starting from 2',5'-di-O-TBDMS-3'-ketouridine 1 or its thymine analogue 2, both xylo (3-10) and ribo (20) epimers of a series of 3"-substituted 3'-spironucleosides have been obtained in good yields and with a total stereoselectivity. Most new compounds were moderately cytotoxic with in some cases slightly selective antiproliferative activities. None of these compounds was active against HIV, but some other antiviral activities against HSV-2, CMV, EBV, or VZV, in the micromolar range, were noted in specific cases.

  DOI：

  10.1080/15257770008035024