1-[2'-deoxy-3'-O-(triisopropylsilyl)-β-D-glycero-tetrofuranosyl]uracil | 355820-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[2'-deoxy-3'-O-(triisopropylsilyl)-β-D-glycero-tetrofuranosyl]uracil
• CAS: 355820-03-0
• 化学式: C₁₇H₃₀N₂O₄Si
• 分子量: 354.522
• InChiKey: YTNGJSCLHZHHIT-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  73.32
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-[2'-deoxy-3'-O-(triisopropylsilyl)-β-D-glycero-tetrofuranosyl]uracil 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 1-(2'-deoxy-β-D-glycero-tetrofuranosyl)-6-[(4,4'-dimethoxytrityloxy)methyl]uracil 3'-[(2-cyanoethyl)diisopropylphosphoramidite]
  参考文献：
  名称：

  具有包含核碱基的主链的寡核苷酸类似物：第 6 部分，2-脱氧-D-赤藓糖衍生的亚磷酰胺：合成和掺入 14-Mer DNA 链

  摘要：

  Two modified DNA 14-mers have been prepared, containing either a 2-deoxy-D-erythrose-derived adenosine analogue carrying a C(8)-CH2O group (deA*). or a 2-deoxy-D-erpthrose-derived uridine analogue, possessing a C(6)-CH2O group (deU*). These nucleosides are linked via a phosphinato group between O-C(3') (deA* and deU*) and O-C(5') of one neighbouring nucleotide, and between C(8)-CH2O (deA*),or C(6)-CH2O (deU*) and O-C(3') of the second neighbour. N-6-Benzoyl-9-(beta -D-erythrofuranosyl)adeine (3) and 1-(beta -D-erythrofuranosyl)uracil (4) were prepared from D-glucose, deoxygenated at C(2'), and converted into the required phosphoramidites 1 and 2. The modified tetradecamers 31 and 32 were prepared by solid-phase synthesis. Pairing studies show a decrease in the melting temperature of 7 to 8 degrees for the duplexes 31 30 and 32 29, as compared to the unmodified DNA duplex 29 30. A comparison with the pairing properties of tetradecamers similarly incorporating deoxyribose- instead of the deoxyerythrose-derived nucleotides evidences that the CH2OH substituent at C(4') has no significant effect on the pairing.

  DOI：

  10.1002/1522-2675(20010516)84:5<1000::aid-hlca1000>3.0.co;2-s
• 作为产物：
  描述：

  2,2'-anhydro-1-(β-D-threofuranosyl)uracil 在 吡啶 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 、 lithium bromide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 30.0h， 生成 1-[2'-deoxy-3'-O-(triisopropylsilyl)-β-D-glycero-tetrofuranosyl]uracil
  参考文献：
  名称：

  具有包含核碱基的主链的寡核苷酸类似物：第 6 部分，2-脱氧-D-赤藓糖衍生的亚磷酰胺：合成和掺入 14-Mer DNA 链

  摘要：

  Two modified DNA 14-mers have been prepared, containing either a 2-deoxy-D-erythrose-derived adenosine analogue carrying a C(8)-CH2O group (deA*). or a 2-deoxy-D-erpthrose-derived uridine analogue, possessing a C(6)-CH2O group (deU*). These nucleosides are linked via a phosphinato group between O-C(3') (deA* and deU*) and O-C(5') of one neighbouring nucleotide, and between C(8)-CH2O (deA*),or C(6)-CH2O (deU*) and O-C(3') of the second neighbour. N-6-Benzoyl-9-(beta -D-erythrofuranosyl)adeine (3) and 1-(beta -D-erythrofuranosyl)uracil (4) were prepared from D-glucose, deoxygenated at C(2'), and converted into the required phosphoramidites 1 and 2. The modified tetradecamers 31 and 32 were prepared by solid-phase synthesis. Pairing studies show a decrease in the melting temperature of 7 to 8 degrees for the duplexes 31 30 and 32 29, as compared to the unmodified DNA duplex 29 30. A comparison with the pairing properties of tetradecamers similarly incorporating deoxyribose- instead of the deoxyerythrose-derived nucleotides evidences that the CH2OH substituent at C(4') has no significant effect on the pairing.

  DOI：

  10.1002/1522-2675(20010516)84:5<1000::aid-hlca1000>3.0.co;2-s