Carbonic acid allyl ester 2-allyloxycarbonyloxy-3-[(2R,3R,4R,5R)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-propyl ester | 853245-50-8

• 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: Carbonic acid allyl ester 2-allyloxycarbonyloxy-3-[(2R,3R,4R,5R)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-propyl ester
• CAS: 853245-50-8
• 化学式: C₂₇H₃₁N₃O₁₂
• 分子量: 589.556
• InChiKey: PZSHDDIVNKDHKD-HAZOKTLASA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  193.97
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Carbonic acid allyl ester 2-allyloxycarbonyloxy-3-[(2R,3R,4R,5R)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-propyl ester 在 二异丙基铵盐四氮唑 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 Carbonic acid allyl ester 2-allyloxycarbonyloxy-3-{(2R,3R,4R,5R)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-tetrahydro-furan-3-yloxy}-propyl ester
  参考文献：
  名称：

  Synthesis of DNA conjugates by solid-phase fragment condensation via aldehyde–nucleophile coupling

  摘要：

  Oligodeoxyribonucletides were synthesized that contain a novel nucleoside, 2'-O-(2,3-dihydroxypropyl)cytidine. Its 2'diol group was blocked by an allyloxycarbonyl protecting group. Selective deprotection of diol group(s) of the support-immobilized blocked oligodcoxyribonucleotide by Pd(0) followed by periodate oxidation resulted in generation of the 2'-aldehyde group(s) on solid-phase. The modified oligonucleotides were used to prepare a number of conjugates with acridine, biotin and N-modified laminin peptides by oxime, hydrazone and hydrazine formation. The method may be applicable to the synthesis of oligonucleotide-peptide conjugates. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.056
• 作为产物：
  描述：

  N-{1-[(2R,3R,3aR,9aR)-3-(2,3-Dihydroxy-propoxy)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 Carbonic acid allyl ester 2-allyloxycarbonyloxy-3-[(2R,3R,4R,5R)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-propyl ester
  参考文献：
  名称：

  Synthesis of DNA conjugates by solid-phase fragment condensation via aldehyde–nucleophile coupling

  摘要：

  Oligodeoxyribonucletides were synthesized that contain a novel nucleoside, 2'-O-(2,3-dihydroxypropyl)cytidine. Its 2'diol group was blocked by an allyloxycarbonyl protecting group. Selective deprotection of diol group(s) of the support-immobilized blocked oligodcoxyribonucleotide by Pd(0) followed by periodate oxidation resulted in generation of the 2'-aldehyde group(s) on solid-phase. The modified oligonucleotides were used to prepare a number of conjugates with acridine, biotin and N-modified laminin peptides by oxime, hydrazone and hydrazine formation. The method may be applicable to the synthesis of oligonucleotide-peptide conjugates. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.056