1'-thymine-(3'-O-t-butyl-diphenylsilyl-6'-carboxamido-2',5',6',7'-tetradeoxy-β-D-ribo-6'-ene-heptofuranosyl) | 172974-50-4

• 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: 1'-thymine-(3'-O-t-butyl-diphenylsilyl-6'-carboxamido-2',5',6',7'-tetradeoxy-β-D-ribo-6'-ene-heptofuranosyl)
• 英文别名: 2-[[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]prop-2-enamide
• CAS: 172974-50-4
• 化学式: C₂₉H₃₅N₃O₅Si
• 分子量: 533.699
• InChiKey: XGARLPBGXPBALP-DSNGMDLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  116.41
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1'-thymine-(3'-O-t-butyl-diphenylsilyl-6'-carboxamido-2',5',6',7'-tetradeoxy-β-D-ribo-6'-ene-heptofuranosyl) 在 N-甲基吗啉 、 吡啶 、 偶氮二异丁腈 、 PIFA 、 三正丁基氢锡 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 甲苯 为溶剂， 反应 19.25h， 生成 benzyl-<1'-(thymin-1-yl)-<9'(S)-benzyloxycarbonylamino-3'-O-t-butyldiphenylsilyl-6'(R,S)-(t-butoxycarbonylamino)-2',5',6',7',8',9'-hexadeoxy>>-β-D-ribo-decofuranuronate
  参考文献：
  名称：

  Total Synthesis of the Thymidine Analogue of Sinefungin

  摘要：

  The carbon skeleton of ''Sinethymidin'' 4 was constructed by two radical coupling reaction. The first step was a coupling of the radical derived from 2 and the unsaturated amide 5. The olefin 6 thus obtained was added to the radical derived from the known N-hydroxy-2-thiopyridinone aspartic ester. ''Sinethymidin'', tested for its antileismanial effect, was devoid of activity.

  DOI：

  10.1080/15257779508009744
• 作为产物：
  描述：

  (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid 、 2-phenylthiomethylacrylamide 在 双硫氧吡啶 、 三苯基膦 作用下， 生成 1-[(2R,4S,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-pyridin-2-ylsulfanyloxolan-2-yl]-5-methylpyrimidine-2,4-dione 、 1'-thymine-(3'-O-t-butyl-diphenylsilyl-6'-carboxamido-2',5',6',7'-tetradeoxy-β-L-ribo-6'-ene-heptofuranosyl) 、 1'-thymine-(3'-O-t-butyl-diphenylsilyl-6'-carboxamido-2',5',6',7'-tetradeoxy-β-D-ribo-6'-ene-heptofuranosyl)
  参考文献：
  名称：

  Total Synthesis of the Thymidine Analogue of Sinefungin

  摘要：

  The carbon skeleton of ''Sinethymidin'' 4 was constructed by two radical coupling reaction. The first step was a coupling of the radical derived from 2 and the unsaturated amide 5. The olefin 6 thus obtained was added to the radical derived from the known N-hydroxy-2-thiopyridinone aspartic ester. ''Sinethymidin'', tested for its antileismanial effect, was devoid of activity.

  DOI：

  10.1080/15257779508009744