3-Benzyloxymethyl-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione | 192653-08-0

• 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: 3-Benzyloxymethyl-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-3-(phenylmethoxymethyl)pyrimidine-2,4-dione
• CAS: 192653-08-0
• 化学式: C₁₈H₂₂N₂O₆
• 分子量: 362.382
• InChiKey: UYGCIYJMVCBASB-ARFHVFGLSA-N

物化性质

• 沸点：
  560.3±60.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  99.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Benzyloxymethyl-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 吡啶 、 咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 3-Benzyloxymethyl-1-[(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: the effect of triazole- and imidazole-modified backbones on DNA/RNA duplex stability

  摘要：

  Thymidine dinucleotide analogs with imidazole-derived backbones (III and IV) were synthesized. These modified dimeric building blocks were incorporated into oligodeoxyribonucleotides. The hybridization affinity of the modified oligonucleotides for RNA complements was determined and compared to the corresponding olefinic modifications I and II. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00270-9
• 作为产物：
  描述：

  苄基氯甲基醚 、 beta-胸苷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到3-Benzyloxymethyl-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: the effect of triazole- and imidazole-modified backbones on DNA/RNA duplex stability

  摘要：

  Thymidine dinucleotide analogs with imidazole-derived backbones (III and IV) were synthesized. These modified dimeric building blocks were incorporated into oligodeoxyribonucleotides. The hybridization affinity of the modified oligonucleotides for RNA complements was determined and compared to the corresponding olefinic modifications I and II. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00270-9

文献信息

• INTERMEDIATES FOR OLIGONUCLEOTIDE SYNTHESIS
  申请人：Novartis AG

  公开号：EP0906327A2

  公开（公告）日：1999-04-07
• US6329519B1
  申请人：——

  公开号：US6329519B1

  公开（公告）日：2001-12-11
• [EN] INTERMEDIATES FOR OLIGONUCLEOTIDE SYNTHESIS<br/>[FR] INTERMEDIAIRES POUR LA SYNTHESE D'OLIGONUCLEOTIDES
  申请人：——

  公开号：WO1997047636A2

  公开（公告）日：1997-12-18

  [EN] A compound of formula (I) where B<1> is a radical of a nucleoside base, R<1> is hydrogen or a hydroxy-protecting group, R<2> is hydrogen, hydroxy or a 2' nucleoside-modifying atom or group, R<3> is an unsubstituted or substituted C1 to C10 alkyl, C2 to C10 alkenyl, C4 to C10 cycloalkylalkyl, C6 to C10 aryl or C7 to C13 aralkyl group, and Z is halogen or a group of formula (II) where R<4> and R<5> are each independently an unsubstituted or substituted C1 to C10 alkyl, C2 to C10 alkenyl, C4 to C10 cycloalkylalkyl, C6 to C10 aryl or C7 to C13 aralkyl group, or R<4> is said group and R<5> is hydrogen, or R<4> and R<5> together with the nitrogen atom to which they are attached denote a five- to thirteen-membered heterocyclic ring, or Z is a group of formula (III): Nuc-O-, where Nuc is the residue of a natural or synthetic nucleoside or oligonucleotide after removal of a 5'-hydroxyl group therefrom attached through a 5' methylene thereof to the indicated oxygen atom.
  [FR] L'invention concerne un composé chimique de la formule (I) dans laquelle B<1> est un radical d'une base nucléosidique, R<1> représente hydrogène ou un groupe inhibant hydroxy, R<2> représente hydrogène, hydroxy ou un atome ou groupe modifiant 2' nucléoside, R<3> représente un groupe alkyle en C1 à C10, alcényle en C2 à C10, cycloalkylalkyle en C4 à C10, aryle en C6 à C10 ou aralkyle en C7 à C13 non substitué ou substitué, et Z représente halogène ou un groupe de la formule (II) dans laquelle R<4> et R<5> représentent chacun, indépendamment, un groupe alkyle en C1 à C10, alcényle en C2 à C10, cycloalkylalkyle en C4 à C10, aryle en C6 à C10 ou aralkyle en C7 à C13 non substitué ou substitué, ou bien R<4> représente ce groupe et R<5> représente hydrogène, ou bien R<4> et R<5>, réunis à l'atome d'azote auquel ils sont liés, représentent un noyau hétérocyclique à cinq ou treize chaînons, ou Z représente un groupe de la formule (III): Nuc-O-, dans laquelle Nuc représente le reste d'un nucléoside ou oligonucléotide naturel ou synthétique après retrait d'un groupe 5'-hydroxyle fixé par un 5'-méthylène à l'atome d'azote précité.
• Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: the effect of triazole- and imidazole-modified backbones on DNA/RNA duplex stability
  作者：Peter von Matt、Karl-Heinz Altmann

  DOI：10.1016/s0960-894x(97)00270-9

  日期：1997.6

  Thymidine dinucleotide analogs with imidazole-derived backbones (III and IV) were synthesized. These modified dimeric building blocks were incorporated into oligodeoxyribonucleotides. The hybridization affinity of the modified oligonucleotides for RNA complements was determined and compared to the corresponding olefinic modifications I and II. (C) 1997 Elsevier Science Ltd.