3,5-di-O-benzyl-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose | 207606-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-di-O-benzyl-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose
• 英文别名: 1,2-di-O-isopropylidene-3,5-di-O-benzyl-3-C-vinyl-α-D-ribofuranose；(3aR,5R,6R,6aR)-6-ethenyl-2,2-dimethyl-6-phenylmethoxy-5-(phenylmethoxymethyl)-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole
• CAS: 207606-87-9
• 化学式: C₂₄H₂₈O₅
• 分子量: 396.483
• InChiKey: PSFUGWYOFWAADQ-JTOYRKQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzyl-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose 在 吡啶 、 甲醇 、 sodium hydroxide 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 139.0h， 生成 1-(3,5-di-O-benzyl-3-C-vinyl-β-D-arabinofuranosyl)thymine
  参考文献：
  名称：

  Christensen, Nanna K.; Petersen, Michael; Nielsen, Poul, Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5458 - 5463

  摘要：

  DOI：
• 作为产物：
  描述：

  5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 23.33h， 生成 3,5-di-O-benzyl-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose
  参考文献：
  名称：

  Christensen, Nanna K.; Petersen, Michael; Nielsen, Poul, Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5458 - 5463

  摘要：

  DOI：

文献信息

• Selective reduction of mono- and disubstituted olefins by NaBH4 and catalytic RuCl3
  作者：Pawan K. Sharma、Surender Kumar、Pawan Kumar、Poul Nielsen

  DOI：10.1016/j.tetlet.2007.10.017

  日期：2007.12

  use of the relatively inexpensive reagent, RuCl3 × H2O, as a catalyst for the reductions of olefins in the presence of water is reported. The combination of cheap and readily available sodium borohydride and a catalytic amount of RuCl3 × H2O selectively reduces mono- and disubstituted olefins, whereas trisubstituted olefins, unless activated, and benzyl ethers remain inert.

  据报道，在水的存在下直接使用相对便宜的试剂RuCl 3  ×H 2 O作为还原烯烃的催化剂。廉价和易于获得的硼氢化钠与催化量的RuCl 3  ×H 2 O的组合可选择性还原单取代和二取代的烯烃，而三取代的烯烃（除非被活化）和苄基醚保持惰性。
• An α-<scp>d</scp>-Configured Bicyclic Nucleoside Restricted in an <i>E</i>-type Conformation:  Synthesis and Parallel RNA Recognition
  作者：Pawan K. Sharma、Michael Petersen、Poul Nielsen

  DOI：10.1021/jo0500380

  日期：2005.6.1

  oxetane ring. The E-type conformation is confirmed by molecular modeling and NMR. The nucleoside is incorporated into short α-DNA sequences. In a mixed pyrimidine context, these recognize complementary parallel RNA-sequences with mainly increased affinity and complementary parallel DNA-sequences with decreased affinity. The present bicyclic analogue represents the first conformationally restricted α-DNA-analogue

  合成了被2'-3'-稠合的氧杂环丁烷环严格限制在E-型构象中的α- d-阿拉伯糖基构型的双环核苷。朝向目标化合物的几种合成策略被描述，并且从成功制备d -木糖衍生物是基于双键的钌-介导的裂解，一个S Ñ 2反转在2-位，得到阿糖-构型，核碱基偶联，最后闭环得到氧杂环丁烷环。该Ë-型构象通过分子建模和NMR确认。核苷被掺入短的α-DNA序列中。在混合的嘧啶环境中，它们识别亲和力主要增加的互补平行RNA序列和亲和力降低的互补平行DNA序列。本双环类似物代表第一个构象受限的α-DNA类似物，以改善与α-DNA单体的混合器中的核酸识别。
• New Ruthenium-Based Protocol for Cleavage of Terminal Olefins to Primary Alcohols:  Improved Synthesis of a Bicyclic Nucleoside
  作者：Pawan K. Sharma、Poul Nielsen

  DOI：10.1021/jo0491861

  日期：2004.8.1

  A new protocol for the oxidative cleavage of terminal alkenes to give exclusively primary alcohols in high yields is introduced. The protocol is based on RuO4-mediated dihydroxylation, NaIO4-mediated diol cleavage, and NaBH4-mediated reduction, but the introduction of a reducing step before the diol cleavage removes the formation of byproducts and improves the yield significantly. The new protocol

  引入了一种新的方案，用于将末端烯烃进行氧化裂解，从而以高收率的方式仅生成伯醇。该方案基于RuO 4介导的二羟基化，NaIO 4介导的二醇裂解和NaBH 4介导的还原，但是在二醇裂解之前引入还原步骤可消除副产物的形成并显着提高产率。已经开发了新的协议，并将其用于改进[3.2.0]双环阿拉伯糖核苷的制备，在反义和反义技术中具有重要的潜力。
• Oligonucleotide analogues
  申请人：Wengel Jesper

  公开号：US20050287566A1

  公开（公告）日：2005-12-29

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。这些核苷酸类似物，即锁定核苷酸类似物（LNAs），能够为寡核苷酸提供与互补RNA和DNA寡聚物的亲和力和特异性方面的有价值的改进。这种新型的LNA修饰的寡核苷酸以及LNA本身在广泛的诊断应用和治疗应用中非常有用。其中包括反义应用、PCR应用、链置换寡聚物、作为核酸聚合酶的底物、作为基于核苷酸的药物等。本发明还涉及这些应用。
• OLIGONUCLEOTIDE ANALOGUES
  申请人：Wengel Jesper

  公开号：US20100279895A1

  公开（公告）日：2010-11-04

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。这些核苷酸类似物，即LNAs（锁定核苷酸类似物），能够为寡核苷酸提供与互补RNA和DNA寡聚物相比亲和力和特异性的有价值的改进。这种新型的LNA修饰的寡核苷酸以及LNAs本身在广泛的诊断应用和治疗应用中都有用途。其中可以提到反义应用、PCR应用、链位移寡聚物、作为核酸聚合酶底物、作为核苷酸基药物等。本发明还涉及这些应用。