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。
• 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
  作者：Poul Nielsen、Jesper Wengel

  DOI：10.1039/a806817h

  日期：——

  A bicyclic thiofuranoside (phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranoside) was efficiently synthesized and introduced as the key synthon in a method for convergent synthesis of α- and β-LNA nucleosides; acid-induced ring-opening reactions of the corresponding bicyclic methyl furanoside are also described.

  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。
• 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.
• 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.