3-Benzyloxymethyl-1-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione | 171762-68-8

• 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: 3-Benzyloxymethyl-1-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 171762-68-8
• 化学式: C₁₉H₂₄N₂O₇
• 分子量: 392.409
• InChiKey: BTTPZAZOOZUSSH-YFHUEUNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  112.15
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-Benzyloxymethyl-1-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 palladium on activated charcoal 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氢气 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 25.0~65.0 ℃ 、101.33 kPa 条件下， 反应 128.0h， 生成 [(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid methyl ester
  参考文献：
  名称：

  An expeditious synthesis of 3′-α-carboxymethyl-2′-O-methyl ribonucleosides

  摘要：

  3'-alpha-Carboxymethyl-2'-O-methyl ribonucleosides, which are important building blocks for the construction of high affinity amide modified antisense oligonucleotides, have been synthesized from the corresponding 2'-O-methyl ribonucleosides via catalytic hydrogenation of their 3'-deoxy 3'-methoxycarbonyl-methylidene derivatives. Reduction of the olefinic double bond proceeds in good to excellent yields and with alpha/beta-product ratios > 9/1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00147-1
• 作为产物：
  描述：

  3-Benzyloxymethyl-1-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-Benzyloxymethyl-1-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  An expeditious synthesis of 3′-α-carboxymethyl-2′-O-methyl ribonucleosides

  摘要：

  3'-alpha-Carboxymethyl-2'-O-methyl ribonucleosides, which are important building blocks for the construction of high affinity amide modified antisense oligonucleotides, have been synthesized from the corresponding 2'-O-methyl ribonucleosides via catalytic hydrogenation of their 3'-deoxy 3'-methoxycarbonyl-methylidene derivatives. Reduction of the olefinic double bond proceeds in good to excellent yields and with alpha/beta-product ratios > 9/1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00147-1