1-[(2R,3R,4R,5R)-3-(3-Dimethylamino-propoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione | 268218-09-3

• 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: 1-[(2R,3R,4R,5R)-3-(3-Dimethylamino-propoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3R,4R,5R)-3-[3-(dimethylamino)propoxy]-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 268218-09-3
• 化学式: C₁₅H₂₅N₃O₆
• 分子量: 343.38
• InChiKey: IUUWKCLJTYGAMP-HKUMRIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(2R,3R,4R,5R)-3-(3-Dimethylamino-propoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 生成 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(3-dimethylamino-propoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  An efficient method for the synthesis of 2′-O-modified nucleosides via double alkylation using cyclic sulfates

  摘要：

  The alkylation of N-3-benzyloxymethyl-5-methyluridine with 1,3,2-dioxathiolane 2,2-dioxide or 1,3,2-dioxathiane 2,2-dioxide resulted in a 2'-O versus 3'-O selectivity of 3:1, respectively. The resulting product has a built-in sulfate leaving group at the terminal end of an ethyl or propyl carbon chain, which can be displaced with sulfur and nitrogen nucleophiles to produce modifications at the 2'-O or 3'-O positions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02329-1
• 作为产物：
  描述：

  N³-benzyloxymethyl-5-methyluridine 在 palladium dihydroxide 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， -45.0~20.0 ℃ 、379.21 kPa 条件下， 生成 1-[(2R,3R,4R,5R)-3-(3-Dimethylamino-propoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  An efficient method for the synthesis of 2′-O-modified nucleosides via double alkylation using cyclic sulfates

  摘要：

  The alkylation of N-3-benzyloxymethyl-5-methyluridine with 1,3,2-dioxathiolane 2,2-dioxide or 1,3,2-dioxathiane 2,2-dioxide resulted in a 2'-O versus 3'-O selectivity of 3:1, respectively. The resulting product has a built-in sulfate leaving group at the terminal end of an ethyl or propyl carbon chain, which can be displaced with sulfur and nitrogen nucleophiles to produce modifications at the 2'-O or 3'-O positions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02329-1

文献信息

• Zwitterionic oligonucleotides with 2′-O-[3-(N,N-dimethylamino)propyl]-RNA modification: synthesis and properties
  作者：Thazha P. Prakash、Muthiah Manoharan、Allister S. Fraser、Andrew M. Kawasaki、Elena A. Lesnik、Stephen R. Owens

  DOI：10.1016/s0040-4039(00)00703-6

  日期：2000.6

  A novel 2'-modification, 2'-O-[3-(N,N-dimethylamino)propyl] or 2'-O-DMAP, has been incorporated into oligonucleotides and compared to the known 2'-O-(3-aminopropyl) or 2'-O-AP modification for antisense properties. The 2'-O-DMAP modified oligonucleotides exhibit very high nuclease resistance like the 2'-O-AP modification due to the 'charge effect' and maintain high binding affinity to target RNA relative to known modifications when a few 2'-O-DMAP residues are dispersed throughout the oligonucleotide. (C) 2000 Elsevier Science Ltd. All rights reserved.