1-[(2R,3R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1,3]dithian-2-yl-3-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione | 257277-51-3

• 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,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1,3]dithian-2-yl-3-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3R,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(1,3-dithian-2-yl)-3-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 257277-51-3
• 化学式: C₃₀H₃₈N₂O₅S₂Si
• 分子量: 598.86
• InChiKey: SOFJWQCQIORJIE-DLGLWYJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(2R,3R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1,3]dithian-2-yl-3-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 silica gel 、 三乙胺 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 57.0h， 生成
  参考文献：
  名称：

  A new approach for the synthesis of 3′-deoxy-3′-C-formyl-ribonucleosides and the synthesis of alternating methylene(methylimino) linked phosphodiester backbone oligonucleotides with 2′-OH and 2′-OMe groups

  摘要：

  A stereoselective synthesis of 3'-deoxy-3'-C-formyl-5-methyluridine 2 is described via the dithiane 4 as the key intermediate. Compound 2 was coupled with 3 into a novel ribo-MMI dimer 1. The dimer was then incorporated into antisense oligonucleotides which were found to have high binding affinity to the target RNA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01814-1
• 作为产物：
  描述：

  5-甲基-1,3-二(三甲基硅烷基)-2,4(1H,3H)-嘧啶二酮 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成 1-[(2R,3R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1,3]dithian-2-yl-3-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  A new approach for the synthesis of 3′-deoxy-3′-C-formyl-ribonucleosides and the synthesis of alternating methylene(methylimino) linked phosphodiester backbone oligonucleotides with 2′-OH and 2′-OMe groups

  摘要：

  A stereoselective synthesis of 3'-deoxy-3'-C-formyl-5-methyluridine 2 is described via the dithiane 4 as the key intermediate. Compound 2 was coupled with 3 into a novel ribo-MMI dimer 1. The dimer was then incorporated into antisense oligonucleotides which were found to have high binding affinity to the target RNA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01814-1

文献信息

• CHIMERIC RNA WITH MODIFIED BACKBONES: ALTERNATING METHYLENE(METHYLIMINO) LINKED PHOSPHODIESTER BACKBONE OLIGONUCLEOTIDES WITH 2′-OH AND 2′-OMe GROUPS
  作者：Marija Prhavc、Balkrishen Bhat、George Just、P. Dan Cook、Muthiah Manoharan

  DOI：10.1081/ncn-100002476

  日期：2001.3.31

  Synthesis of a novel ribo-MMI dimer with 2'-OH and 2'-OMe in 5'- and 3'-nucleosides, respectively is presented. The synthesis was accomplished by reductive coupling of 3'-deoxy-3'-C-formyluridine and 2'-O-methyl-5'-O-methylaminouridine via a thioacetal as the key intermediate for the top part of the dimer. Incorporation of ribo-MMI dimers into oligonucleotides increased binding affinity for target RNA.