(3''R)-1-[2',5'-bis(O-tert-butyldimethylsilyl)-3'-deoxy-β-D-xylofuranosyl]uracil-3'-spiro-2''-(3''-carbamoyloxirane) | 272780-80-0

• 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''-carbamoyloxirane)
• 英文别名: (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-carboxamide；(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-carboxamide
• CAS: 272780-80-0
• 化学式: C₂₃H₄₁N₃O₇Si₂
• 分子量: 527.765
• InChiKey: ORAHAOMNMKUNSC-IDMCENKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  7

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''-carbamoyloxirane) 在 sodium azide 、 氯化铵 作用下， 以 乙二醇甲醚 为溶剂， 反应 45.0h， 以66%的产率得到1-[2-O-tert-butyldimethylsilyl-3-C-[(1S)-2-amino-1-azido-2-oxoethyl]-β-D-xylofuranosyl]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：

  (3''-R)-1-[2',5'-bis(O-tert-butyldimethylsilyl)-3'-deoxy-β-D-xylofuranosyl]uracil-3'-spiro-2''-(3''-methoxycarbonyloxirane) 在 氨 作用下， 以 甲醇 为溶剂， 以90%的产率得到(3''R)-1-[2',5'-bis(O-tert-butyldimethylsilyl)-3'-deoxy-β-D-xylofuranosyl]uracil-3'-spiro-2''-(3''-carbamoyloxirane)
  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

文献信息

• Highly Stereoselective Synthesis and Biological Properties of Nucleoside Analogues Bearing a Spiro Inserted Oxirane Ring
  作者：Jean M. J. Tronchet、Imre Kovacs、Michel Seman、Pierre Dilda、Erik De Clercq、Jan Balzarini

  DOI：10.1080/15257770008035024

  日期：2000.4

  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.