[(2S,4R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxy-dihydro-furan-(3E)-ylidene]-acetic acid methyl ester | 221536-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S,4R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxy-dihydro-furan-(3E)-ylidene]-acetic acid methyl ester
• CAS: 221536-78-3
• 化学式: C₃₈H₄₄N₂O₈Si
• 分子量: 684.861
• InChiKey: XBQREEDHZSNZJH-KOJSFIJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  107.22
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  [(2S,4R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxy-dihydro-furan-(3E)-ylidene]-acetic acid methyl ester 在 palladium on activated charcoal 吡啶 、 1H-1,2,4-三唑 、 盐酸 、 lithium hydroxide 、 ammonium hydroxide 、 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 74.0h， 生成 ((2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-{5-methyl-4-[1-methyl-pyrrolidin-(2Z)-ylideneamino]-2-oxo-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-5-methyl-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 71.0h， 生成 [(2S,4R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxy-dihydro-furan-(3E)-ylidene]-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