2,3'-anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-1-(β-D-threo-pentofuranosyl)uracil | 124288-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,3'-anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-1-(β-D-threo-pentofuranosyl)uracil
• 英文别名: 2,3'-anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxyuridine；(1R,9R,10R)-10-[[tert-butyl(dimethyl)silyl]oxymethyl]-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-5-one
• CAS: 124288-67-1
• 化学式: C₁₅H₂₄N₂O₄Si
• 分子量: 324.452
• InChiKey: GRCMIIHREXFDGU-NQBHXWOUSA-N

物化性质

• 熔点：
  180-190 °C (decomp)
• 沸点：
  372.1±52.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3'-anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-1-(β-D-threo-pentofuranosyl)uracil 在 四乙基氟化铵水合物 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以65%的产率得到(2R)-3t-hydroxymethyl-2,3-dihydro-2r,5c-methano-pyrimido[2,1-b][1,5,3]dioxazepin-9-one
  参考文献：
  名称：

  Joshi, Bhalchandra V.; Rao, T. Sudhakar; Reese, Colin B., Journal of the Chemical Society. Perkin transactions I, 1992, # 19, p. 2537 - 2544

  摘要：

  DOI：
• 作为产物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-2'-deoxyuridine 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以68%的产率得到2,3'-anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-1-(β-D-threo-pentofuranosyl)uracil
  参考文献：
  名称：

  一锅法合成含有 α-氨基膦酸酯部分的新型 2'-脱氧尿苷衍生物

  摘要：

  已经从 5'-O-叔丁基二甲基甲硅烷基-3'-氨基-2', 3'-双脱氧尿苷以良好的收率制备了一系列 2'-脱氧尿苷 (8a-k) 的 α-氨基膦酸酯衍生物。所有产物的结构均经1H NMR、31P NMR、31C NMR、IR光谱、质谱和元素分析确证。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:230–235, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20288

  DOI：

  10.1002/hc.20288

文献信息

• A Facile One-Pot Synthesis of 2,3'-Anhydro-2'-Deoxyuridines via 3'-O-Imidazolylsulfonates
  作者：No、Dong Seong Shin、Bok Ju Song、Ahn、Ha

  DOI：10.1080/00397910008086944

  日期：2000.11

  Continued interests in the novel synthetic methods of the pivotal compound, 2,3'-anhydro-2'-deoxyribonucleosides (7) uncovered a facile one-pot conversion of 5 with 1,1'-sulfonyldiimidazole in basic conditions to 7 with almost quantitative yields (91-99%).
• Synthesis, antiretrovirus effects and phosphorylation kinetics of 3'-isocyano-3'-deoxythymidine and 3'-isocyano-2',3'-dideoxyuridine
  作者：Johann Hiebl、Erich Zbiral、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00164a059

  日期：1990.2

  The silylated AzddThd 5 and AzddUrd 6 prepared from 2,3'-anhydronucleoside derivatives 3 and 4 were transformed to formamides 7 and 8 by using the sequence RN3----RN = P(C6H5)----RNHCHO. Formamides 7 and 8 were dehydrated to the protected 3'-isocyano derivatives 9 and 10; deblocking gave 11 and 12. Neither 3'-isocyano-3'-deoxythymidine (11) nor 3'-isocyano-2',3'-dideoxyuridine (12) showed anti-HIV activity at noncytotoxic concentrations. ddThd derivative 11 was considerably more toxic to MT-4 cells than ddUrd derivative 12; it also had a much greater affinity (Ki) for MT-4 cell dThd kinase than ddUrd derivative 12. Both compounds appear to be linear mixed-type inhibitors of MT-4 cell dThd kinase.
• HIEBL, JOHANN;ZBIRAL, ERICH;BALZARINI, JAN;DE, CLERCQ ERIK, J. MED. CHEM., 33,(1990) N, C. 845-848
  作者：HIEBL, JOHANN、ZBIRAL, ERICH、BALZARINI, JAN、DE, CLERCQ ERIK

  DOI：——

  日期：——
• One-pot synthesis of novel 2′-deoxyuridine derivatives containing α-aminophosphonate moieties
  作者：Zhi-Qiang Shang、Ru-Yu Chen、You Huang

  DOI：10.1002/hc.20288

  日期：2007.4

  A series of α-aminophosphonate derivatives of 2′-deoxyuridine (8a–k) have been prepared from 5′-O-tert-butyldimethylsilyl-3′-amino-2′, 3′-dideoxyuridine in good yields. The structures of all the products were confirmed by 1H NMR, 31P NMR, 31C NMR, and IR spectroscopy, and mass spectrometry and elemental analyses. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:230–235, 2007; Published online in Wiley

  已经从 5'-O-叔丁基二甲基甲硅烷基-3'-氨基-2', 3'-双脱氧尿苷以良好的收率制备了一系列 2'-脱氧尿苷 (8a-k) 的 α-氨基膦酸酯衍生物。所有产物的结构均经1H NMR、31P NMR、31C NMR、IR光谱、质谱和元素分析确证。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:230–235, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20288
• Joshi, Bhalchandra V.; Rao, T. Sudhakar; Reese, Colin B., Journal of the Chemical Society. Perkin transactions I, 1992, # 19, p. 2537 - 2544
  作者：Joshi, Bhalchandra V.、Rao, T. Sudhakar、Reese, Colin B.

  DOI：——

  日期：——