Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester | 188404-22-0

• 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: Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester
• CAS: 188404-22-0
• 化学式: C₂₀H₂₂N₂O₉
• 分子量: 434.403
• InChiKey: VZUYJESZIBOGGV-RWNSOOOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  138.31
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  The synthesis and binding properties of oligonucleotide analogs containing diastereomerically pure conformationally restricted acetal linkages

  摘要：

  The synthesis of 5,6-bicyclic thymine:thymine nucleoside containing a conformationally restricted dioxane acetal has been achieved from 2'-O-allyl 5-methyl uridine. The two diastereomers were separated and incorporated in a single position within an oligonucleotide (ON) sequence. The binding properties of these ONs when hybridized to complementary RNA and DNA were evaluated by thermal denaturation (Tm) analysis. Lower Tms for both diastereomers were obtained when compared to the corresponding control phosphodiester ON. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00607-5
• 作为产物：
  描述：

  2'-O-allyl-5-methyl uridine 在 吡啶 、 sodium periodate 、 四氧化锇 、 甲酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester
  参考文献：
  名称：

  The synthesis and binding properties of oligonucleotide analogs containing diastereomerically pure conformationally restricted acetal linkages

  摘要：

  The synthesis of 5,6-bicyclic thymine:thymine nucleoside containing a conformationally restricted dioxane acetal has been achieved from 2'-O-allyl 5-methyl uridine. The two diastereomers were separated and incorporated in a single position within an oligonucleotide (ON) sequence. The binding properties of these ONs when hybridized to complementary RNA and DNA were evaluated by thermal denaturation (Tm) analysis. Lower Tms for both diastereomers were obtained when compared to the corresponding control phosphodiester ON. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00607-5