methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside | 219854-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside
• 英文别名: [(2S,3S,4R)-4-hydroxy-5-methoxy-3-phenylmethoxy-2-(phenylmethoxymethyl)oxolan-2-yl]methyl methanesulfonate
• CAS: 219854-35-0
• 化学式: C₂₂H₂₈O₈S
• 分子量: 452.526
• InChiKey: CAXTVCWOCOUTOC-PUZDIZQLSA-N

物化性质

• 沸点：
  630.2±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside 在 水 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranose
  参考文献：
  名称：

  Synthesis and chemoselective activation of phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-1-thio-β-d-ribofuranoside: a key synthon towards α-LNA

  摘要：

  一种双环硫呋喃苷（苯基3,5-二-O-苄基-2-O,4-C-亚甲基-β-D-核糖呋喃苷）被高效合成并作为α-和β-LNA核苷的聚合合成中的关键合成物引入；还描述了相应双环甲基呋喃苷的酸诱导开环反应。

  DOI：

  10.1039/a806817h
• 作为产物：
  描述：

  1,2-O-(异丙亚基)-4-C-[(苯基甲氧基)甲基]-3-O-(苯基甲基)-beta-L-来苏呋喃糖 在 吡啶 、 盐酸 、 水 作用下， 生成 methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and chemoselective activation of phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-1-thio-β-d-ribofuranoside: a key synthon towards α-LNA

  摘要：

  一种双环硫呋喃苷（苯基3,5-二-O-苄基-2-O,4-C-亚甲基-β-D-核糖呋喃苷）被高效合成并作为α-和β-LNA核苷的聚合合成中的关键合成物引入；还描述了相应双环甲基呋喃苷的酸诱导开环反应。

  DOI：

  10.1039/a806817h

文献信息

• α-LNA, locked nucleic acid with α-d-configuration
  作者：Poul Nielsen、Jakob Kragh Dalskov

  DOI：10.1039/b003104f

  日期：——

  The bicyclic thymine monomer of α-LNA (αTL) was efficiently synthesised and used in the synthesis of α-LNA sequences: incorporation of single αTL-monomers in α-configured oligothymidylates destabilises the affinity towards both complementary DNA and RNA, whereas a fully modified α-LNA sequence displays a very efficient recognition of complementary RNA.

  有效合成了α-LNA的双环胸腺嘧啶单体（αTL），并用于合成α-LNA序列：在α-配置的寡胸腺苷酸中加入单个αTL单体会降低对互补DNA和RNA的亲和力，而完全改性的α-LNA序列对互补RNA表现出非常高效的识别能力。
• α-LNA (Locked Nucleic Acid withα-D-Configuration): Synthesis and Selective Parallel Recognition of RNA
  作者：Poul Nielsen、Nanna K. Christensen、Jakob K. Dalskov

  DOI：10.1002/1521-3765(20020201)8:3<712::aid-chem712>3.0.co;2-0

  日期：2002.2.1

  alpha-LNA is presented as a stereoisomer of LNA (locked nucleic acid) with alpha-D-configuration. Three different approaches towards the thymine a-LNA monomer as well as the 5-methylcytosine alpha-LNA monomer are presented. Different alpha-LNA sequences have been synthesised and their hybridisation with complementary DNA and RNA has been evaluated by means of thermal stability experiments and circular dichroism spectroscopy. In a mixed pyrimidine sequence, alpha-LNA displays unprecedented parallel-stranded and selective RNA binding. Furthermore, a remarkable selectivity for hybridisation with RNA over DNA is indicated.
• SYNTHESIS AND EVALUATION OF α-LNA
  作者：Nanna K. Christensen、Jakob K. Dalskov、Paul Nielsen

  DOI：10.1081/ncn-100002438

  日期：2001.3.31

  Three different synthetic routes to the alpha -configured LNA thymine monomer starting from D-allose or D-arabinose were investigated. The introduction of one or four alpha -LNA monomers into alpha -DNA had a destabilizing effect on the duplexes. However, a fully modified alpha -LNA sequence displayed strong recognition of complementary RNA, but no transition with DNA.
• Synthesis of Abasic Locked Nucleic Acid and Two <i>seco</i>-LNA Derivatives and Evaluation of Their Hybridization Properties Compared with Their More Flexible DNA Counterparts
  作者：Lisbet Kværnø、Ravindra Kumar、Britta M. Dahl、Carl Erik Olsen、Jesper Wengel

  DOI：10.1021/jo000275x

  日期：2000.8.1

  To investigate the structural basis of the unique hybridization properties of LNA (locked nucleic acid) three novel LNA derivatives with modified carbohydrate parts were synthesized and evaluated with respect to duplex stabilities. The abasic LNA monomer (X(L), Figure 1) with the rigid carbohydrate moiety of LNA but no nucleobase attached showed no enhanced duplex stabilities compared to its more flexible abasic DNA counterpart (X, Figure 1). These results suggest that the exceptional hybridization properties of LNA primarily originate from improved intrastrand nucleobase stacking and not backbone preorganization. Two monocyclic seco-LNA derivatives, obtained by cleavage of the C1'-O4' bond of an LNA monomer or complete removal of the O4'-furanose oxygen atom (Z(L) and dZ(L), respectively, Figure 1), were compared to their acyclic DNA counterpart (Z, Figure 1). Even though they are more constrained than Z, the seco-LNA derivatives Z(L) and dZ(L) destabilize duplex formation even more than the flexible seco-DNA monomer Z.
• A New Synthetic Approach Towards α- and β-LNA (Locked Nucleic Acids)
  作者：Poul Nielsen、Jesper Wengel

  DOI：10.1080/15257779908041546

  日期：1999.4

  A bicyclo[2.2.1] phenyl thioglycoside was efficiently synthesised and introduced as the key synthon in a novel method for convergent synthesis of beta-LNA-nucleosides as well as their alpha-configurated isomers. An acid-induced ring-opening reaction on the corresponding bicyclo[2.2.1] methyl furanoside is also described.