methyl (E,4R)-4-[(1R)-1-(2,4-dioxopyrimidin-1-yl)-2-phenylselanylethoxy]-5-trityloxypent-2-enoate | 263557-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl (E,4R)-4-[(1R)-1-(2,4-dioxopyrimidin-1-yl)-2-phenylselanylethoxy]-5-trityloxypent-2-enoate
• CAS: 263557-34-2
• 化学式: C₃₇H₃₄N₂O₆Se
• 分子量: 681.647
• InChiKey: FLPOMGIFNVYACB-IKNNIZKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (E,4R)-4-[(1R)-1-(2,4-dioxopyrimidin-1-yl)-2-phenylselanylethoxy]-5-trityloxypent-2-enoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 [(2R,3S,5R)-5-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl]-acetic acid methyl ester 、 [(2R,3R,5R)-5-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl]-acetic acid methyl ester 、 (1R,9S,10R)-3,5-Dioxo-10-trityloxymethyl-11-oxa-2,4-diaza-tricyclo[7.2.1.0^2,7]dodecane-8-carboxylic acid methyl ester
  参考文献：
  名称：

  Radical-mediated furanose ring reconstruction from 2′,3′- seco -uridine

  摘要：

  Starting from 5'-O-trityl-2',3'-seco-uridine, reconstruction of a furanose structure was carried out by the following sequence of reactions: (I) regioselective introduction of a phenylselenenyl group to the 2'-position of the 2',3'-seco-uridine, (2) oxidation and subsequent Wittig reaction of the 3'-hydroxyl group and (3) intramolecular radical reaction (5-exo-trig ring closure) leading to 3'-C-carbon-substituted 2',3 '-dideoxyuridine. Also studied is the Pummerer reaction of the 2'-phenylseleno derivative of 2',3'-seco-uridine. The resulting product, an alpha-(acyloxy)phenylselenide, also serves as a substrate for the radical cyclization to allow the introduction of a hydroxyl group at the 2'-position of the reconstructed furanose ring. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00203-4
• 作为产物：
  描述：

  [(2R)-2-[(1R)-1-(2,4-dioxopyrimidin-1-yl)-2-phenylselanylethoxy]-3-trityloxypropyl] methanesulfonate 在 草酰氯 、 氨 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 45.25h， 生成 methyl (E,4R)-4-[(1R)-1-(2,4-dioxopyrimidin-1-yl)-2-phenylselanylethoxy]-5-trityloxypent-2-enoate
  参考文献：
  名称：

  Radical-mediated furanose ring reconstruction from 2′,3′- seco -uridine

  摘要：

  Starting from 5'-O-trityl-2',3'-seco-uridine, reconstruction of a furanose structure was carried out by the following sequence of reactions: (I) regioselective introduction of a phenylselenenyl group to the 2'-position of the 2',3'-seco-uridine, (2) oxidation and subsequent Wittig reaction of the 3'-hydroxyl group and (3) intramolecular radical reaction (5-exo-trig ring closure) leading to 3'-C-carbon-substituted 2',3 '-dideoxyuridine. Also studied is the Pummerer reaction of the 2'-phenylseleno derivative of 2',3'-seco-uridine. The resulting product, an alpha-(acyloxy)phenylselenide, also serves as a substrate for the radical cyclization to allow the introduction of a hydroxyl group at the 2'-position of the reconstructed furanose ring. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00203-4

文献信息

• Radical-mediated furanose ring reconstruction from 2′,3′- seco -uridine
  作者：Hiroki Kumamoto、Junko Ogamino、Hiromichi Tanaka、Hisaki Suzuki、Kazuhiro Haraguchi、Tadashi Miyasaka、Tsutomu Yokomatsu、Shiroshi Shibuya

  DOI：10.1016/s0040-4020(01)00203-4

  日期：2001.4

  Starting from 5'-O-trityl-2',3'-seco-uridine, reconstruction of a furanose structure was carried out by the following sequence of reactions: (I) regioselective introduction of a phenylselenenyl group to the 2'-position of the 2',3'-seco-uridine, (2) oxidation and subsequent Wittig reaction of the 3'-hydroxyl group and (3) intramolecular radical reaction (5-exo-trig ring closure) leading to 3'-C-carbon-substituted 2',3 '-dideoxyuridine. Also studied is the Pummerer reaction of the 2'-phenylseleno derivative of 2',3'-seco-uridine. The resulting product, an alpha-(acyloxy)phenylselenide, also serves as a substrate for the radical cyclization to allow the introduction of a hydroxyl group at the 2'-position of the reconstructed furanose ring. (C) 2001 Elsevier Science Ltd. All rights reserved.