9-(2-O-acetyl-β-D-arabinofuranosyl)-N²-phenoxyacetylguanine | 169886-77-5

• 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: 9-(2-O-acetyl-β-D-arabinofuranosyl)-N²-phenoxyacetylguanine
• 英文别名: [(2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-[6-oxo-2-[(2-phenoxyacetyl)amino]-3H-purin-9-yl]oxolan-3-yl] acetate
• CAS: 169886-77-5
• 化学式: C₂₀H₂₁N₅O₈
• 分子量: 459.415
• InChiKey: BLQFUGPOWVGSOE-ZSKVKKPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.68
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  177.89
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  9-(2-O-acetyl-β-D-arabinofuranosyl)-N²-phenoxyacetylguanine 在 咪唑 、 三乙胺 、 三氯化磷 作用下， 生成 9-(2-O-acetyl-5-O-monomethoxytrityl-β-D-arabinofuranosyl)-N²-phenoxyacetylguanine
  参考文献：
  名称：

  Building Blocks for Synthesis of Oligoarabinonucleotides: Preparation of Arabinonucleoside H-Phosphonates from Protected Ribonucleosides

  摘要：

  A straightforward and inexpensive synthesis of arabinonucleoside H-phosphonates has been developed. Arabinonucleosides were synthesised from protected ribonucleosides via 2'-keto derivatives. Reaction conditions have been optimised for compounds bearing labile N-protections. Further protecting group manipulation and phosphonylation gave the required H-phosphonate monomers.

  DOI：

  10.1080/15257779508010720
• 作为产物：
  描述：

  N-(苯氧基乙酰基)-3',5'-O-[1,1,3,3-四(异丙基)-1,3-二硅氧烷二基]鸟苷 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 戴斯-马丁氧化剂 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 9-(2-O-acetyl-β-D-arabinofuranosyl)-N²-phenoxyacetylguanine
  参考文献：
  名称：

  Building Blocks for Synthesis of Oligoarabinonucleotides: Preparation of Arabinonucleoside H-Phosphonates from Protected Ribonucleosides

  摘要：

  A straightforward and inexpensive synthesis of arabinonucleoside H-phosphonates has been developed. Arabinonucleosides were synthesised from protected ribonucleosides via 2'-keto derivatives. Reaction conditions have been optimised for compounds bearing labile N-protections. Further protecting group manipulation and phosphonylation gave the required H-phosphonate monomers.

  DOI：

  10.1080/15257779508010720

文献信息

• Synthesis of Oligoarabinonucleotides Using H-Phosphonates
  作者：Eriks Rozners、Roger Strömberg、Erika Bizdena

  DOI：10.1080/15257779508012487

  日期：1995.5.1

  Protected arabinonucleoside H-phosphonates have been prepared starting from ribonucleosides and used in solid phase synthesis of oligoarabinonucleotides.