Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester | 186839-95-2

• 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: Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester
• 英文别名: [(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]-3-oxooxolan-2-yl]methyl 2-bromoacetate
• CAS: 186839-95-2
• 化学式: C₂₅H₃₃BrN₂O₈Si
• 分子量: 597.535
• InChiKey: DFQXBWVVBDPWDF-SXSPYAJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester 在 palladium dihydroxide samarium diiodide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 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：

  3-Benzyloxymethyl-1-[(2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 在 2,6-二甲基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester
  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

• 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).