methyl 1-(2,3,5-tri-O-t-butyldimethylsilyl-β-D-ribofuranosyl)imidazolin-2-one-4-carboxylate | 704890-69-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: methyl 1-(2,3,5-tri-O-t-butyldimethylsilyl-β-D-ribofuranosyl)imidazolin-2-one-4-carboxylate
• 英文别名: methyl 3-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-2-oxo-1H-imidazole-5-carboxylate
• CAS: 704890-69-7
• 化学式: C₂₈H₅₆N₂O₇Si₃
• 分子量: 617.018
• InChiKey: YYVSATQIPMICAM-SSGKUCQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 1-(2,3,5-tri-O-t-butyldimethylsilyl-β-D-ribofuranosyl)imidazolin-2-one-4-carboxylate 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-(2,3,5-tri-O-t-butyldimethylsilyl-β-D-ribofuranosyl)imidazolin-2-one-4-carboxaldehyde
  参考文献：
  名称：

  Synthesis of 4‐Formyl‐4‐imidazolin‐2‐one Nucleosides, Isomers of Uridine and 2′‐Deoxyuridine

  摘要：

  The syntheses of the ribo- and deoxyribonucleoside derivatives of 4-formyl-4-imidazolin-2-one, isosteric isomers of uridine and 2'-deoxyuridine, respectively, were carried out by ring contraction of the corresponding 5-bromouracil nucleosides, followed by conversion of the carboxyl side-chain of the products to the respective carboxaldehyde derivatives.

  DOI：

  10.1081/ncn-120027837
• 作为产物：
  描述：

  1-(β-D-Ribofuranosyl)-2-oxo-Δ⁴-imidazolin-4-carbonsaeure 在 咪唑 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 1-(2,3,5-tri-O-t-butyldimethylsilyl-β-D-ribofuranosyl)imidazolin-2-one-4-carboxylate
  参考文献：
  名称：

  Synthesis of 4‐Formyl‐4‐imidazolin‐2‐one Nucleosides, Isomers of Uridine and 2′‐Deoxyuridine

  摘要：

  The syntheses of the ribo- and deoxyribonucleoside derivatives of 4-formyl-4-imidazolin-2-one, isosteric isomers of uridine and 2'-deoxyuridine, respectively, were carried out by ring contraction of the corresponding 5-bromouracil nucleosides, followed by conversion of the carboxyl side-chain of the products to the respective carboxaldehyde derivatives.

  DOI：

  10.1081/ncn-120027837

文献信息

• Synthesis of 4‐Formyl‐4‐imidazolin‐2‐one Nucleosides, Isomers of Uridine and 2′‐Deoxyuridine
  作者：Xiang‐Jun Jiang、Thomas I. Kalman

  DOI：10.1081/ncn-120027837

  日期：2004.1.1

  The syntheses of the ribo- and deoxyribonucleoside derivatives of 4-formyl-4-imidazolin-2-one, isosteric isomers of uridine and 2'-deoxyuridine, respectively, were carried out by ring contraction of the corresponding 5-bromouracil nucleosides, followed by conversion of the carboxyl side-chain of the products to the respective carboxaldehyde derivatives.