5'-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribose | 68703-51-5

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribose
• 英文别名: 5-O-((1,1-Dimethylethyl)dimethylsilyl)-2,3-O-(1-methylethylidene)-D-ribose；(4R,5R)-5-[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 68703-51-5
• 化学式: C₁₄H₂₈O₅Si
• 分子量: 304.459
• InChiKey: XNPICRPLWJBSLX-GRYCIOLGSA-N

物化性质

• 熔点：
  50-51°C
• 沸点：
  100-102°C/1 mm
• 密度：
  1.049±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷和乙酸乙酯。
• 稳定性/保质期：
  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  5'-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribose 在 四氯化碳 、 三(二甲胺基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 5'-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribose chloride
  参考文献：
  名称：

  Fluorine Substituted Adenosines As Probes of Nucleobase Protonation in Functional RNAs

  摘要：

  Ionized nucleobases are required for folding, conformational switching, or catalysis in a number of functional RNAs. A common strategy to study these sites employs nucleoside analogues with perturbed pK(a), but the interpretation of these studies is often complicated by the chemical modification introduced, in particular modifications that add, remove, or translocate hydrogen bonding groups in addition to perturbing pKa values. In the present study we present a series of fluorine substituted adenosine analogues that produce large changes in N1 pK(a) values with minimal structural perturbation. These analogues include fluorine for hydrogen substitutions in the adenine ring of adenosine and 7-deaza-adenosine with resulting N1 pK(a) values spanning more than 4 pKa units. To demonstrate the utility of these analogues we have conducted a nucleotide analogue interference mapping (NAIM) study on a self-ligating construct of the Varkud Satellite (VS) ribozyme. We find that each of the analogues is readily incorporated by T7 RNA polymerase and produces fully active transcripts when substituted at the majority of sites. Strong interferences are observed for three sites known to be critical for VS ribozyme function, most notably A756. Substitutions at A756 lead to slight enhancements in activity for elevated pK(a) analogues and dramatic interferences in activity for reduced pK(a) analogues, supporting the proposed catalytic role for this base. The structural similarity of these analogues, combined with their even incorporation and selective interference, provides an improved method for identifying sites of adenosine protonation in a variety of systems.

  DOI：

  10.1021/ja803336y
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 2,3-O-isopropylidene-D-ribose 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以89%的产率得到5'-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribose
  参考文献：
  名称：

  Chiron方法立体选择性全合成鸟油醇A

  摘要：

  使用D-核糖作为手性前体，可以完成立体式合成鼠李素A（一种二羟基化的四氢吡喃化合物）的立体控制。涉及的关键步骤是芳基格氏反应，立体选择性烷氧基指导的酮还原以及分子内氧迈克尔的加成。

  DOI：

  10.1002/hlca.200900342

文献信息

• Stereoselective Total Synthesis of Goniothalesdiol A via Chiron Approach
  作者：Jhillu S. Yadav、Ragam Nageshwar Rao、Ragam Somaiah、Valaboju Harikrishna、Basi V. Subba Reddy

  DOI：10.1002/hlca.200900342

  日期：——

  The stereocontrolled synthesis of goniothalesdiol A, a dihydroxylated tetrahydropyran compound, has been accomplished using D‐ribose as chiral precursor. The key steps involved are aryl Grignard reaction, stereoselective alkoxy‐directed keto reduction, and intramolecular oxy‐Michael addition.

  使用D-核糖作为手性前体，可以完成立体式合成鼠李素A（一种二羟基化的四氢吡喃化合物）的立体控制。涉及的关键步骤是芳基格氏反应，立体选择性烷氧基指导的酮还原以及分子内氧迈克尔的加成。
• Fluorine Substituted Adenosines As Probes of Nucleobase Protonation in Functional RNAs
  作者：Ian T. Suydam、Scott A. Strobel

  DOI：10.1021/ja803336y

  日期：2008.10.15

  Ionized nucleobases are required for folding, conformational switching, or catalysis in a number of functional RNAs. A common strategy to study these sites employs nucleoside analogues with perturbed pK(a), but the interpretation of these studies is often complicated by the chemical modification introduced, in particular modifications that add, remove, or translocate hydrogen bonding groups in addition to perturbing pKa values. In the present study we present a series of fluorine substituted adenosine analogues that produce large changes in N1 pK(a) values with minimal structural perturbation. These analogues include fluorine for hydrogen substitutions in the adenine ring of adenosine and 7-deaza-adenosine with resulting N1 pK(a) values spanning more than 4 pKa units. To demonstrate the utility of these analogues we have conducted a nucleotide analogue interference mapping (NAIM) study on a self-ligating construct of the Varkud Satellite (VS) ribozyme. We find that each of the analogues is readily incorporated by T7 RNA polymerase and produces fully active transcripts when substituted at the majority of sites. Strong interferences are observed for three sites known to be critical for VS ribozyme function, most notably A756. Substitutions at A756 lead to slight enhancements in activity for elevated pK(a) analogues and dramatic interferences in activity for reduced pK(a) analogues, supporting the proposed catalytic role for this base. The structural similarity of these analogues, combined with their even incorporation and selective interference, provides an improved method for identifying sites of adenosine protonation in a variety of systems.