3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione | 186839-91-8

• 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: 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-3-(phenylmethoxymethyl)pyrimidine-2,4-dione
• CAS: 186839-91-8
• 化学式: C₂₉H₄₈N₂O₇Si₂
• 分子量: 592.88
• InChiKey: BQYHMMMXXXMZIZ-VNSJUHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 在 palladium dihydroxide 吡啶 、 2,6-二甲基吡啶 、 chromium(VI) oxide 、 molecular sieve 、 samarium diiodide 、 氢气 、 乙酸酐 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-[(2R,3R,3aR,7aR)-3-(tert-Butyl-dimethyl-silanyloxy)-3a-hydroxy-5-oxo-hexahydro-furo[2,3-c]pyran-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Nucleosides and Nucleotides. 163. Synthesis of 3‘-β-Branched Uridine Derivatives via Intramolecular Reformatsky-Type Reaction Promoted by Samarium Diiodide¹

  摘要：

  A novel efficient method for the synthesis of 3'-beta-branched uridines starting from uridine was developed, in which a SmI2-promoted intramolecular Reformatsky-type reaction was effectively used. 5'-O-(Bromoacetyl)-3'-ketouridine derivatives 12, 26, and 27 were synthesized from uridine and were subjected to an intramolecular Reformatsky-type reaction. When 12, 26, and 27 were treated with 2.0 equiv of SmI2 in THF at -78 degrees C, intramolecular carbon-carbon bond formation at the 3'-beta-position proceeded smoothly to give the corresponding 3',5'-lactones 14, 28, and 29 in high yields, respectively. Treatment of 28 with NH3/MeOH gave the 3'-beta-branched uridine derivative 32 quantitatively, which was then deprotected to give 3'-C-(carbamoylmethyl)uridine (33).

  DOI：

  10.1021/jo961665f
• 作为产物：
  描述：

  苄基氯甲基醚 在 吡啶 、 silver nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Nucleosides and Nucleotides. 163. Synthesis of 3‘-β-Branched Uridine Derivatives via Intramolecular Reformatsky-Type Reaction Promoted by Samarium Diiodide¹

  摘要：

  A novel efficient method for the synthesis of 3'-beta-branched uridines starting from uridine was developed, in which a SmI2-promoted intramolecular Reformatsky-type reaction was effectively used. 5'-O-(Bromoacetyl)-3'-ketouridine derivatives 12, 26, and 27 were synthesized from uridine and were subjected to an intramolecular Reformatsky-type reaction. When 12, 26, and 27 were treated with 2.0 equiv of SmI2 in THF at -78 degrees C, intramolecular carbon-carbon bond formation at the 3'-beta-position proceeded smoothly to give the corresponding 3',5'-lactones 14, 28, and 29 in high yields, respectively. Treatment of 28 with NH3/MeOH gave the 3'-beta-branched uridine derivative 32 quantitatively, which was then deprotected to give 3'-C-(carbamoylmethyl)uridine (33).

  DOI：

  10.1021/jo961665f

文献信息

• Synthetic Studies towards the Identification of Novel Capuramycin Analogs with Mycobactericidal Activity
  作者：Michio Kurosu、Kai Li

  DOI：10.3987/com-08-s(f)38

  日期：——

  Expeditious syntheses of capuramycin, an effective MraY inhibitor in vivo, analogs are described. Synthetic schemes reported here are extremely useful for the generation of capuramycin analogs to identify minimum structure requirement to exhibit antimycobactericidal activity.
• Nucleosides and Nucleotides. 163. Synthesis of 3‘-β-Branched Uridine Derivatives via Intramolecular Reformatsky-Type Reaction Promoted by Samarium Diiodide¹
  作者：Satoshi Ichikawa、Satoshi Shuto、Noriaki Minakawa、Akira Matsuda

  DOI：10.1021/jo961665f

  日期：1997.3.1

  A novel efficient method for the synthesis of 3'-beta-branched uridines starting from uridine was developed, in which a SmI2-promoted intramolecular Reformatsky-type reaction was effectively used. 5'-O-(Bromoacetyl)-3'-ketouridine derivatives 12, 26, and 27 were synthesized from uridine and were subjected to an intramolecular Reformatsky-type reaction. When 12, 26, and 27 were treated with 2.0 equiv of SmI2 in THF at -78 degrees C, intramolecular carbon-carbon bond formation at the 3'-beta-position proceeded smoothly to give the corresponding 3',5'-lactones 14, 28, and 29 in high yields, respectively. Treatment of 28 with NH3/MeOH gave the 3'-beta-branched uridine derivative 32 quantitatively, which was then deprotected to give 3'-C-(carbamoylmethyl)uridine (33).