1,2-O-isopropylidene-3-C-(prop-1-en-3-yl)-3,5-di-O-benzyl-α-D-ribofuranose | 191163-48-1

• 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: 1,2-O-isopropylidene-3-C-(prop-1-en-3-yl)-3,5-di-O-benzyl-α-D-ribofuranose
• 英文别名: (3aR,5R,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-5-(phenylmethoxymethyl)-6-prop-2-enyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole
• CAS: 191163-48-1
• 化学式: C₂₅H₃₀O₅
• 分子量: 410.51
• InChiKey: PHUXOYROHQAMFH-STAYPELNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  1,2-O-isopropylidene-3-C-(prop-1-en-3-yl)-3,5-di-O-benzyl-α-D-ribofuranose 在 palladium dihydroxide 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium methylate 、 sodium hydride 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 3-[[(3aR,4R,6R,6aS)-4-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-6-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,4,6,6a-tetrahydro-2H-furo[2,3-c]furan-3a-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  A novel class of conformationally restricted oligonucleotide analogues: synthesis of 2′,3′-bridged monomers and RNA-selective hybridisation

  摘要：

  一种新的2′,3′-双环核苷5已被合成并融入寡核苷酸类似物中，从而实现对RNA互补序列的强选择性结合。

  DOI：

  10.1039/a608231i
• 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 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,2-O-isopropylidene-3-C-(prop-1-en-3-yl)-3,5-di-O-benzyl-α-D-ribofuranose
  参考文献：
  名称：

  A novel class of conformationally restricted oligonucleotide analogues: synthesis of 2′,3′-bridged monomers and RNA-selective hybridisation

  摘要：

  一种新的2′,3′-双环核苷5已被合成并融入寡核苷酸类似物中，从而实现对RNA互补序列的强选择性结合。

  DOI：

  10.1039/a608231i

文献信息

• A novel class of conformationally restricted oligonucleotide analogues: synthesis of 2′,3′-bridged monomers and RNA-selective hybridisation
  作者：Poul Nielsen、Henrik M. Pfundheller、Jesper Wengel

  DOI：10.1039/a608231i

  日期：——

  A novel 2′,3′-bicyclic nucleoside 5 has been synthesised and incorporated into oligonucleotide analogues resulting in strong and selective binding to an RNA complement.

  一种新的2′,3′-双环核苷5已被合成并融入寡核苷酸类似物中，从而实现对RNA互补序列的强选择性结合。
• Synthesis of an Adenine Nucleoside Containing the (8′<i>R</i>) Epimeric Carbohydrate Core of Amipurimycin and Its Biological Study
  作者：Rajendra S. Mane、Sougata Ghosh、Balu A. Chopade、Oliver Reiser、Dilip D. Dhavale

  DOI：10.1021/jo102193q

  日期：2011.4.15

  The (8′R) epimeric carbohydrate core 2 of amipurimycin was synthesized from d-glucose derived allylic alcohol 3 in 11 steps and 13% overall yield. The key steps involve an acid-catalyzed acetonide ring opening of 9 with concomitant formation of an unprecedented pyranose ring skeleton to give 2,7-dioxabicyclo[3.2.1]octane 10. The α-orientation of the furan ring in 10 readily allows the stereoselective

  所述（8' - [R ）差向异构体的碳水化合物芯2 amipurimycin的合成自d葡萄糖衍生的烯丙醇3在11个步骤和13％的总收率。的关键步骤涉及酸催化的丙酮化合物开环9与伴随形成了前所未有的吡喃糖环骨架，得到2,7-二氧杂双环[3.2.1]辛烷的10。呋喃环在10中的α取向很容易实现呋喃糖环的立体选择性β-糖基化和打开，这在去除保护基团后即可得到吡喃糖基腺嘌呤核苷2。研究了2种的抗真菌和抗癌活性。
• 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。
• Oligonucleotide Analogues
  申请人：WENGEL Jesper

  公开号：US20110245327A1

  公开（公告）日：2011-10-06

  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 ( L ocked N ucleoside A nalogues), 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。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有价值的改进，使其对互补的RNA和DNA寡聚体具有更高的亲和力和特异性。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很有用。其中包括反义应用、PCR应用、链置换寡聚体、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。