(1S,3S,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane | 1160728-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3S,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane
• 英文别名: 1-[(1S,3S,4S,7R)-1-(hydroxymethyl)-7-phenylmethoxy-2-oxa-5-azabicyclo[2.2.1]heptan-3-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1160728-66-4
• 化学式: C₁₈H₂₁N₃O₅
• 分子量: 359.382
• InChiKey: MVCNBVWRXPVHQA-KPEUIFRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105.58
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,3S,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane 、 三氟乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到(1S,3S,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-5-aza-2-oxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Parallel RNA-strand recognition by 2′-amino-β-l-LNA

  摘要：

  A short synthetic route to the first beta-L-ribo configured locked nucleic acid (LNA), that is, 2'-amino-beta-L-LNA thymine phosphoramidite 6, has been developed from bicyclic nucleoside 1. Incorporation of 2'-amino-beta-L-LNA thymine monomers into alpha-DNA strands results in probes forming stable duplexes with complementary RNA in parallel orientation. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.079
• 作为产物：
  描述：

  [(1S,3S,4S,7R)-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-7-phenylmethoxy-2-oxa-5-azabicyclo[2.2.1]heptan-1-yl]methyl benzoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 42.0h， 以5.29 g的产率得到(1S,3S,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Parallel RNA-strand recognition by 2′-amino-β-l-LNA

  摘要：

  A short synthetic route to the first beta-L-ribo configured locked nucleic acid (LNA), that is, 2'-amino-beta-L-LNA thymine phosphoramidite 6, has been developed from bicyclic nucleoside 1. Incorporation of 2'-amino-beta-L-LNA thymine monomers into alpha-DNA strands results in probes forming stable duplexes with complementary RNA in parallel orientation. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.079