[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole) | 859210-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)
• 英文别名: tert-butyl 3-[(5R,6S,8R,9R)-4-amino-9-[tert-butyl(dimethyl)silyl]oxy-2,2-dioxo-6-(phenylmethoxymethyl)-7-oxa-2lambda6-thia-1-azaspiro[4.4]non-3-en-8-yl]-5-methyl-2,6-dioxopyrimidine-1-carboxylate；tert-butyl 3-[(5R,6S,8R,9R)-4-amino-9-[tert-butyl(dimethyl)silyl]oxy-2,2-dioxo-6-(phenylmethoxymethyl)-7-oxa-2λ6-thia-1-azaspiro[4.4]non-3-en-8-yl]-5-methyl-2,6-dioxopyrimidine-1-carboxylate
• CAS: 859210-62-1
• 化学式: C₃₀H₄₄N₄O₉SSi
• 分子量: 664.852
• InChiKey: DXLFJHYFQYTROD-AADRLYINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  175
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole) 在 palladium dihydroxide 、 potassium carbonate 、 环己烯 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 41.0h， 生成 1-[(5R,6S,8R,9R)-4-Amino-9-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dioxo-7-oxa-2λ⁶-thia-1-aza-spiro[4.4]non-3-en-8-yl]-3-ethyl-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  First Synthesis and Evaluation of the Inhibitory Effects of Aza Analogues of TSAO on HIV-1 Replication

  摘要：

  Aza TSAO-T derivatives bearing a dihydroisothiazole dioxide ring instead of an oxathiole dioxide ring at the C-3 ' position on the sugar moiety were prepared. We have synthesized four families of compounds depending on substitution at both N-3 and N-2 ''. Biological evaluation showed that these compounds are HIV-1(IIIB)-specific and potent reverse transcriptase inhibitors with EC50 values between 0.13 and 3.5 mu M in cell culture.

  DOI：

  10.1021/jm050091g
• 作为产物：
  描述：

  1-(3'-amino-5'-O-benzyl-2'-O-tert-butyldimethylsilyl-3'-C-cyano-3'-deoxy-3'-N-mesyl-β-D-ribofuranosyl)thymine 在 吡啶 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 [1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)
  参考文献：
  名称：

  First Synthesis and Evaluation of the Inhibitory Effects of Aza Analogues of TSAO on HIV-1 Replication

  摘要：

  Aza TSAO-T derivatives bearing a dihydroisothiazole dioxide ring instead of an oxathiole dioxide ring at the C-3 ' position on the sugar moiety were prepared. We have synthesized four families of compounds depending on substitution at both N-3 and N-2 ''. Biological evaluation showed that these compounds are HIV-1(IIIB)-specific and potent reverse transcriptase inhibitors with EC50 values between 0.13 and 3.5 mu M in cell culture.

  DOI：

  10.1021/jm050091g

文献信息

• First Synthesis and Evaluation of the Inhibitory Effects of Aza Analogues of TSAO on HIV-1 Replication
  作者：Albert Nguyen Van Nhien、Cyrille Tomassi、Christophe Len、José Luis Marco-Contelles、Jan Balzarini、Christophe Pannecouque、Erik De Clercq、Denis Postel

  DOI：10.1021/jm050091g

  日期：2005.6.1

  Aza TSAO-T derivatives bearing a dihydroisothiazole dioxide ring instead of an oxathiole dioxide ring at the C-3 ' position on the sugar moiety were prepared. We have synthesized four families of compounds depending on substitution at both N-3 and N-2 ''. Biological evaluation showed that these compounds are HIV-1(IIIB)-specific and potent reverse transcriptase inhibitors with EC50 values between 0.13 and 3.5 mu M in cell culture.