3'-[N-(tert-butoxycarbonyl)-O-methyl-L-tyrosyl]amido-3'-deoxyinosine | 946497-29-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3'-[N-(tert-butoxycarbonyl)-O-methyl-L-tyrosyl]amido-3'-deoxyinosine
• 英文别名: tert-butyl N-[(2S)-1-[[(2S,3S,4R,5R)-4-hydroxy-2-(hydroxymethyl)-5-(6-oxo-1H-purin-9-yl)oxolan-3-yl]amino]-3-(4-methoxyphenyl)-1-oxopropan-2-yl]carbamate
• CAS: 946497-29-6
• 化学式: C₂₅H₃₂N₆O₈
• 分子量: 544.564
• InChiKey: MEYRBTQNYDMNER-PXBBLBRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  186
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-[N-(tert-butoxycarbonyl)-O-methyl-L-tyrosyl]amido-3'-deoxyinosine 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.75h， 以80%的产率得到3'-(O-methyl-L-tyrosyl)amido-3'-deoxyinosine
  参考文献：
  名称：

  Facile and Rapid Access to Inosine Puromycin Analogues through the Use of Adenylate Deaminase

  摘要：

  To study the ribosomal peptidyl transfer, puromycin analogues are of interest in which adenine has been replaced by hypoxanthine. We synthesized inosine puromycin analogues from 3'-azidodeoxyadenosine derivatives using adenylate deaminase for the quantitative transformation of the N-heterocycle. The amino acid coupling was carried out under Staudinger-Vilarrasa conditions in 94% yield starting from the protected and in 82% using the unprotected azide, thus, in the presence of two hydroxyls and a lactam function.

  DOI：

  10.1021/ol070818q
• 作为产物：
  描述：

  3'-azido-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine 在 phosphate buffer 、 三丁基膦 、 四丁基氟化铵 、 1-羟基苯并三唑 、 达卡巴嗪 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 生成 3'-[N-(tert-butoxycarbonyl)-O-methyl-L-tyrosyl]amido-3'-deoxyinosine
  参考文献：
  名称：

  Facile and Rapid Access to Inosine Puromycin Analogues through the Use of Adenylate Deaminase

  摘要：

  To study the ribosomal peptidyl transfer, puromycin analogues are of interest in which adenine has been replaced by hypoxanthine. We synthesized inosine puromycin analogues from 3'-azidodeoxyadenosine derivatives using adenylate deaminase for the quantitative transformation of the N-heterocycle. The amino acid coupling was carried out under Staudinger-Vilarrasa conditions in 94% yield starting from the protected and in 82% using the unprotected azide, thus, in the presence of two hydroxyls and a lactam function.

  DOI：

  10.1021/ol070818q

文献信息

• Facile and Rapid Access to Inosine Puromycin Analogues through the Use of Adenylate Deaminase
  作者：Adib Charafeddine、Hubert Chapuis、Peter Strazewski

  DOI：10.1021/ol070818q

  日期：2007.7.1

  To study the ribosomal peptidyl transfer, puromycin analogues are of interest in which adenine has been replaced by hypoxanthine. We synthesized inosine puromycin analogues from 3'-azidodeoxyadenosine derivatives using adenylate deaminase for the quantitative transformation of the N-heterocycle. The amino acid coupling was carried out under Staudinger-Vilarrasa conditions in 94% yield starting from the protected and in 82% using the unprotected azide, thus, in the presence of two hydroxyls and a lactam function.