1-{5-O-(4-chlorobenzoyl)-2,3-di-O-isobutyryl-3-C-[2-(trimethylsilyl)ethynyl]-β-D-ribopentofuranosyl}cytosine | 199787-45-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-{5-O-(4-chlorobenzoyl)-2,3-di-O-isobutyryl-3-C-[2-(trimethylsilyl)ethynyl]-β-D-ribopentofuranosyl}cytosine
• 英文别名: 1-[5-O-(4-chlorobenzoyl)-2,3-DI-O-ISOBUTYRYL-3-C-(2-trimethylsilylethynyl)-β-D-ribofuranosyl]cytosine；[(2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-bis(2-methylpropanoyloxy)-3-(2-trimethylsilylethynyl)oxolan-2-yl]methyl 4-chlorobenzoate
• CAS: 199787-45-6
• 化学式: C₂₉H₃₆ClN₃O₈Si
• 分子量: 618.159
• InChiKey: CIBYMUVYIZTGLE-KBADEGBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-{5-O-(4-chlorobenzoyl)-2,3-di-O-isobutyryl-3-C-[2-(trimethylsilyl)ethynyl]-β-D-ribopentofuranosyl}cytosine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以68%的产率得到乙炔基胞苷
  参考文献：
  名称：

  Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-d-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction

  摘要：

  A practical synthetic route to the antitumor nucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, 1) from 1,2-O-isopropylidene-D-xylofuranose (3) has been developed. Since most of the compounds were obtained as crystals, the target ECyd was prepared without any chromatographic purification in 31% overall yield from compound 3. The isobutyryloxy group was found to be an effective leaving group at the anomeric position of the 3-beta-C-ethynyl glycosyl donors in the key Vorbruggen glycosylation reaction. Using a similar procedure without chromatographic purification, the uracil congener EUrd [1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)uracil (2), which also has a potent antitumor effect, was synthesized from 3 in 39% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01249-2
• 作为产物：
  描述：

  N-(三甲基硅基)-2-(三甲基硅氧基)-4-嘧啶胺 、 5-O-(4-chlorobenzoyl)-1,2,3-tri-O-isobutyryl-3-C-[2-(trimethylsilyl)ethynyl]-D-ribo-pentofuranose 在 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以81%的产率得到1-{5-O-(4-chlorobenzoyl)-2,3-di-O-isobutyryl-3-C-[2-(trimethylsilyl)ethynyl]-β-D-ribopentofuranosyl}cytosine
  参考文献：
  名称：

  Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-d-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction

  摘要：

  A practical synthetic route to the antitumor nucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, 1) from 1,2-O-isopropylidene-D-xylofuranose (3) has been developed. Since most of the compounds were obtained as crystals, the target ECyd was prepared without any chromatographic purification in 31% overall yield from compound 3. The isobutyryloxy group was found to be an effective leaving group at the anomeric position of the 3-beta-C-ethynyl glycosyl donors in the key Vorbruggen glycosylation reaction. Using a similar procedure without chromatographic purification, the uracil congener EUrd [1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)uracil (2), which also has a potent antitumor effect, was synthesized from 3 in 39% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01249-2