5-[(benzyloxy)methyl]-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine | 304849-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-[(benzyloxy)methyl]-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine
• 英文别名: 5-benzyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine；1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-(phenylmethoxymethyl)pyrimidine-2,4-dione
• CAS: 304849-85-2
• 化学式: C₃₈H₃₈N₂O₈
• 分子量: 650.728
• InChiKey: FLUQOWNUZSJRDR-BMPTZRATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 5-[(benzyloxy)methyl]-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以92%的产率得到5-benzyloxymethyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine 3'-(N,N-diisopropyl)-2-cyanoethyl phosphoramidite
  参考文献：
  名称：

  Aromaticvs. Carbohydrate Residues in the Major Groove: Synthesis of 5-[(Benzyloxy)methyl]pyrimidine Nucleosides and Their Incorporation into Oligonucleotides

  摘要：

  The synthesis of 5-[(benzyloxy)methyl]-substituted pyrimidine 2'-deoxynucleosides 14 and 15 starting from the uracil derivative 6 and tetra-O-acetyl-D-ribose is described (Schemes 1-3). These nucleosides were converted to the corresponding cyanoethyl phosphoramidites 18 and 19, respectively, and incorporated into oligodeoxynucleotide decamers. The 5-[(benzyloxy)methyl]-nucleoside building blocks T-bo(d) and C-bom(d) (bo = benzyloxy, bom = (benzyloxy)methyl) - shape analogs of the naturally occurring glucosylated nucleosides 1 and 2 (see Fig. 1) - lead to weaker binding affinities of oligodeoxynucleotides pairing to DNA as well as RNA complements. The modification is more destabilizing in the case of T-bo(d) than C-bom(d). Analysis of the thermodynamics of duplex formation shows that T-bo(d) and C-bom(d), incorporation leads to a smaller entropy change in duplex formation that is, however, overcompensated by a less Favorable enthalpy term. Molecular-modeling studies suggest that the benzyl groups reside in the major groove which would explain the improved pairing entropy as a result of the exclusion of ordered H2O.

  DOI：

  10.1002/1522-2675(20000809)83:8<1962::aid-hlca1962>3.0.co;2-8
• 作为产物：
  描述：

  四乙酰核糖 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,O-双三甲硅基乙酰胺 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 63.58h， 生成 5-[(benzyloxy)methyl]-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine
  参考文献：
  名称：

  Aromaticvs. Carbohydrate Residues in the Major Groove: Synthesis of 5-[(Benzyloxy)methyl]pyrimidine Nucleosides and Their Incorporation into Oligonucleotides

  摘要：

  The synthesis of 5-[(benzyloxy)methyl]-substituted pyrimidine 2'-deoxynucleosides 14 and 15 starting from the uracil derivative 6 and tetra-O-acetyl-D-ribose is described (Schemes 1-3). These nucleosides were converted to the corresponding cyanoethyl phosphoramidites 18 and 19, respectively, and incorporated into oligodeoxynucleotide decamers. The 5-[(benzyloxy)methyl]-nucleoside building blocks T-bo(d) and C-bom(d) (bo = benzyloxy, bom = (benzyloxy)methyl) - shape analogs of the naturally occurring glucosylated nucleosides 1 and 2 (see Fig. 1) - lead to weaker binding affinities of oligodeoxynucleotides pairing to DNA as well as RNA complements. The modification is more destabilizing in the case of T-bo(d) than C-bom(d). Analysis of the thermodynamics of duplex formation shows that T-bo(d) and C-bom(d), incorporation leads to a smaller entropy change in duplex formation that is, however, overcompensated by a less Favorable enthalpy term. Molecular-modeling studies suggest that the benzyl groups reside in the major groove which would explain the improved pairing entropy as a result of the exclusion of ordered H2O.

  DOI：

  10.1002/1522-2675(20000809)83:8<1962::aid-hlca1962>3.0.co;2-8

文献信息

• Aromaticvs. Carbohydrate Residues in the Major Groove: Synthesis of 5-[(Benzyloxy)methyl]pyrimidine Nucleosides and Their Incorporation into Oligonucleotides
  作者：Reto Bertolini、Jürg Hunziker

  DOI：10.1002/1522-2675(20000809)83:8<1962::aid-hlca1962>3.0.co;2-8

  日期：2000.8.9

  The synthesis of 5-[(benzyloxy)methyl]-substituted pyrimidine 2'-deoxynucleosides 14 and 15 starting from the uracil derivative 6 and tetra-O-acetyl-D-ribose is described (Schemes 1-3). These nucleosides were converted to the corresponding cyanoethyl phosphoramidites 18 and 19, respectively, and incorporated into oligodeoxynucleotide decamers. The 5-[(benzyloxy)methyl]-nucleoside building blocks T-bo(d) and C-bom(d) (bo = benzyloxy, bom = (benzyloxy)methyl) - shape analogs of the naturally occurring glucosylated nucleosides 1 and 2 (see Fig. 1) - lead to weaker binding affinities of oligodeoxynucleotides pairing to DNA as well as RNA complements. The modification is more destabilizing in the case of T-bo(d) than C-bom(d). Analysis of the thermodynamics of duplex formation shows that T-bo(d) and C-bom(d), incorporation leads to a smaller entropy change in duplex formation that is, however, overcompensated by a less Favorable enthalpy term. Molecular-modeling studies suggest that the benzyl groups reside in the major groove which would explain the improved pairing entropy as a result of the exclusion of ordered H2O.
• Megied, Ahmed E.-S. Abdel; Ali, Omar M.; Kofoed, Thomas, Nucleosides and nucleotides, 2001, vol. 20, # 1-2, p. 1 - 10
  作者：Megied, Ahmed E.-S. Abdel、Ali, Omar M.、Kofoed, Thomas、Pedersen, Erik B.

  DOI：——

  日期：——