N1-(2,3-dideoxy-3-(S)-C-dimethylphosphono-5-O-benzoyl-β-D-ribofuranosyl)-thymine | 161821-86-9

• 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: N1-(2,3-dideoxy-3-(S)-C-dimethylphosphono-5-O-benzoyl-β-D-ribofuranosyl)-thymine
• 英文别名: [(2R,3S,5R)-3-dimethoxyphosphoryl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 161821-86-9
• 化学式: C₁₉H₂₃N₂O₈P
• 分子量: 438.374
• InChiKey: NWNWGBWTNVOVRC-OWCLPIDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N1-(2,3-dideoxy-3-(S)-C-dimethylphosphono-5-O-benzoyl-β-D-ribofuranosyl)-thymine 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以55%的产率得到N1-(2,3-dideoxy-3-C-dimethylphosphono-β-D-ribofuranosyl)-thymine
  参考文献：
  名称：

  3′-C-phosphonates as nucleotides analogues synthesis starting from original C-phosphonosugars (in ribo- and deoxyribo- series)

  摘要：

  3-C-phosphonosugars were synthetised starting from 2-deoxy-D-ribose and alpha-D-xylofuranose via the Pudovic reaction followed by reduction. Their condensation with nucleobases (thymine and adenine) gave original 3'-C-phosphononucleosides in ribo- and 2-deoxyribo- series, with a stereocontrol of the reactions.

  DOI：

  10.1016/s0040-4020(01)85564-2
• 作为产物：
  描述：

  N1-(2-O-acetyl-3-deoxy-3-C-dimethylphosphono-5-O-benzoyl-β-D-ribofuranosyl)-thymine 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 一水合肼 作用下， 以 吡啶 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 26.0h， 生成 N1-(2,3-dideoxy-3-(S)-C-dimethylphosphono-5-O-benzoyl-β-D-ribofuranosyl)-thymine
  参考文献：
  名称：

  3′-C-phosphonates as nucleotides analogues synthesis starting from original C-phosphonosugars (in ribo- and deoxyribo- series)

  摘要：

  3-C-phosphonosugars were synthetised starting from 2-deoxy-D-ribose and alpha-D-xylofuranose via the Pudovic reaction followed by reduction. Their condensation with nucleobases (thymine and adenine) gave original 3'-C-phosphononucleosides in ribo- and 2-deoxyribo- series, with a stereocontrol of the reactions.

  DOI：

  10.1016/s0040-4020(01)85564-2

文献信息

• [EN] 3'-PHOSPHONONUCLEOSIDE COMPOUNDS AND METHOD FOR PREPARING SAME<br/>[FR] COMPOSES 3'-PHOSPHONONUCLEOSIDES ET PROCEDE DE PREPARATION
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：WO1995011252A1

  公开（公告）日：1995-04-27

  (EN) A method for preparing a compound of formula (Ia), wherein B is a purine or pyrimidine base, X is H or OH, and Y is H, OH or CH3, by (1) condensation reacting a pentose compound (II) with a protected purine or pyrimidine base B' to give a protected compound (I') in accordance with formulae (II) and (I'), wherein X' is H or OR'', where R'' is an OH function protective grouping, B' is the base B with optionally protected exocyclic functions NH2, Z is a leaving group such as a halogen or an OR group, and R and R' are OH function protective groupings; and (2) deprotecting the compound (I').(FR) La présente invention a pour objet un procédé de préparation d'un composé de formule (Ia) dans laquelle: B représente une base purique ou pyrimidique; X est H ou OH; Y est H, OH ou CH3; caractérisé en ce que (1) on effectue une réaction de condensation d'un composé pentose (II) avec une base purique ou pyrimidique protégée B' pour obtenir un composé protégé (I') selon les formules (II) et (I') dans lesquelles X' représente H ou OR', R' étant un groupement protecteur de la fonction OH; B' représente la base B dont les fonctions exocycliques NH2 sont, le cas échéant, protégées; Z est un groupe partant tel qu'un halogène ou un groupe OR; R et R' sont des groupements protecteurs de la fonction OH, et (2) on déprotège le composé (I').
• 3′-C-phosphonates as nucleotides analogues synthesis starting from original C-phosphonosugars (in ribo- and deoxyribo- series)
  作者：Corine Serra、Georges Dewynter、Jean-Louis Montero、Jean-Louis Imbach

  DOI：10.1016/s0040-4020(01)85564-2

  日期：1994.1

  3-C-phosphonosugars were synthetised starting from 2-deoxy-D-ribose and alpha-D-xylofuranose via the Pudovic reaction followed by reduction. Their condensation with nucleobases (thymine and adenine) gave original 3'-C-phosphononucleosides in ribo- and 2-deoxyribo- series, with a stereocontrol of the reactions.