(+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(o-xylylenephosphate) ribonucleoside | 250699-13-9

• 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: (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(o-xylylenephosphate) ribonucleoside
• 英文别名: 1-[(3aS,4R,6R,6aR)-2,2-dimethyl-6-[(3-oxido-1,5-dihydro-2,4,3-benzodioxaphosphepin-3-ium-3-yl)oxymethyl]-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-3-(phenylmethoxymethyl)pyrimidine-2,4-dione
• CAS: 250699-13-9
• 化学式: C₂₉H₃₃N₂O₉P
• 分子量: 584.563
• InChiKey: RRTNZEQUDBVSRE-RSQMYVMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(o-xylylenephosphate) ribonucleoside 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (-)-β-D-carbocyclic-1'-(1H-uracil-1-yl) ribonucleoside monophosphate
  参考文献：
  名称：

  Synthesis of Chiral Carbocyclic Ribonucleotides

  摘要：

  The carbocyclic analogs of CMP, UMP, GMP, IMP, and ribo-TMP, of the same absolute configuration as the naturally occurring beta-D-ribofuranose-based ribonucleoside monophosphates, have been synthesized. The synthetic route employed Mitsunobu coupling of the heterocycles, appropriately protected where necessary, with a differentially protected, chiral carbocyclic core.

  DOI：

  10.1080/07328319908044853
• 作为产物：
  描述：

  (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside 在 四氮唑 、 四丁基氟化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(o-xylylenephosphate) ribonucleoside
  参考文献：
  名称：

  Synthesis of Chiral Carbocyclic Ribonucleotides

  摘要：

  The carbocyclic analogs of CMP, UMP, GMP, IMP, and ribo-TMP, of the same absolute configuration as the naturally occurring beta-D-ribofuranose-based ribonucleoside monophosphates, have been synthesized. The synthetic route employed Mitsunobu coupling of the heterocycles, appropriately protected where necessary, with a differentially protected, chiral carbocyclic core.

  DOI：

  10.1080/07328319908044853