6-(hydroxymethyl)-2',3'-O-isopropylideneuridine | 325705-75-7

• 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: 6-(hydroxymethyl)-2',3'-O-isopropylideneuridine
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-(hydroxymethyl)pyrimidine-2,4-dione
• CAS: 325705-75-7
• 化学式: C₁₃H₁₈N₂O₇
• 分子量: 314.295
• InChiKey: LIOPVBVXOSGMLR-QCNRFFRDSA-N

物化性质

• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  123.01
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-(hydroxymethyl)-2',3'-O-isopropylideneuridine 在 水 、 戴斯-马丁氧化剂 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 <3S,4S,5R-(1β,3β,4aα,7aα,13aβ)>-1,4,4a,7a,8,13a-hexahydro-1-hydroxy-6,6-dimethyl-3,13a:4,8-diepoxy-3H,6H-dioxolano<4,5-f>pyrimido<6,1-c><1,4>oxazonine-10,12(11H,13H)-dione
  参考文献：
  名称：

  The 5′,6-Oxomethylene Transglycosidic Tether for Conformational Restriction of Pyrimidine Ribonucleosides. Investigation of 6-Formyl- and 6-(Hydroxymethyl)uridine 5′-Carboxaldehydes

  摘要：

  In an effort to develop a new motif for the transglycosidic tethering of the pyrimidine nucleoside framework, the 2',3'-O-isopropylidenated and unprotected versions of 6-formyl- and 6-(hydroxymethyl)uridine 5'-carboxaldehyde were prepared and these were examined for their ability to adopt 5',6-oxomethylene tethered solution structures. In aqueous solution, the 2',3'-O-isopropylidenated nucleosides readily generated spiro-dihydrouridines via proximity-induced transglycosidic intramolecular reactions. In stark contrast, their unprotected counterparts existed mainly as the untethered aldehyde hydrates. Based on these findings, the 5',6-oxomethylene transglycosidic tether appears to constitute a useful conformational restriction motif for the pyrimidine ribonucleoside flamework, but only when the 5'-OH group is functionalized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00970-4
• 作为产物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-6-(hydroxymethyl)-2',3'-O-isopropylideneuridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以89%的产率得到6-(hydroxymethyl)-2',3'-O-isopropylideneuridine
  参考文献：
  名称：

  The 5′,6-Oxomethylene Transglycosidic Tether for Conformational Restriction of Pyrimidine Ribonucleosides. Investigation of 6-Formyl- and 6-(Hydroxymethyl)uridine 5′-Carboxaldehydes

  摘要：

  In an effort to develop a new motif for the transglycosidic tethering of the pyrimidine nucleoside framework, the 2',3'-O-isopropylidenated and unprotected versions of 6-formyl- and 6-(hydroxymethyl)uridine 5'-carboxaldehyde were prepared and these were examined for their ability to adopt 5',6-oxomethylene tethered solution structures. In aqueous solution, the 2',3'-O-isopropylidenated nucleosides readily generated spiro-dihydrouridines via proximity-induced transglycosidic intramolecular reactions. In stark contrast, their unprotected counterparts existed mainly as the untethered aldehyde hydrates. Based on these findings, the 5',6-oxomethylene transglycosidic tether appears to constitute a useful conformational restriction motif for the pyrimidine ribonucleoside flamework, but only when the 5'-OH group is functionalized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00970-4

文献信息

• Oligonucleotide Analogues with a‘Nucleobase-Including Backbone’. Part 10
  作者：Andrew John Matthews、Punit Kumar Bhardwaj、Andrea Vasella

  DOI：10.1002/hlca.200490204

  日期：2004.9

  fully deprotected dimer 32 proved insufficiently soluble in CDCl3. This observation strongly evidences that structural differentiation of oligonucleotides and their analogues into backbone and nucleobases is not required for pairing. The dinucleotide analogues were prepared by O-alkylation of C(8)-unsubstituted or of C(8)-oxymethylated, partially protected adenosines by the C(6)-mesyloxy- or C(6)-halomethylated

  的二核苷类似物24，25，28 - 30，和33在CDCl准3溶液。由尿苷部分的HN（3）的浓度依赖性化学位移和热力学参数确定的缔合常数为265 M -1（33）至3220 M -1（30）。CDCl 3中的31缔合太强而无法确定（与浓度无关的δ（HN（3））约为12.8 ppm），并且完全脱保护的二聚体32被证明不足以溶于CDCl 3。该观察结果有力证明配对不需要寡核苷酸及其类似物结构分化为骨架和核碱基。通过制备的二核苷酸类似物Ô烷基化的C（8）未被取代的或C（8） -oxymethylated，部分保护的腺苷由C（6） -mesyloxy-或C（6） -halomethylated尿苷20 - 22，随后通过部分或全部脱保护。