3,5-di-O-benzyl-2-deoxy-β-D-ribofuranosyl cyanide | 170983-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-di-O-benzyl-2-deoxy-β-D-ribofuranosyl cyanide
• 英文别名: 3,5-Di-O-benzyl-1-cyano-2-desoxy-β-D-ribofuranose；1β-cyano-3,5-di-O-benzyl-1,2-dideoxy-D-ribofuranose；3,5-di-O-benzyl-1-cyano-2-deoxy-β-D-ribose；(2R,4S,5R)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolane-2-carbonitrile
• CAS: 170983-98-9
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: FWPAZJDISPEIPR-HSALFYBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzyl-2-deoxy-β-D-ribofuranosyl cyanide 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 16.34h， 生成 4-[(E)-2-(2-deoxy-3,5-di-O-benzyl-β-D-ribofuranos-1-yl)vinyl]-1-tritylimidazole
  参考文献：
  名称：

  Synthesis of C4-Linked C0- and C2-Imidazole 2′-Deoxyribonucleoside Phos­phoramidites and Imidazole Base-Pairing Effects on DNA

  摘要：

  The synthesis of C4-linked imidazole C-0- and C-2-2'-deoxyribonucleoside phosphoramidites (dPAs), in which the final phosphitylations are greatly improved by 4,5-dicyanoimidazole-promoted conversion, is described. The respective dPAs are successfully incorporated into the sequence of a 15-nt DNA, and the abilities of one or two imidazoles to pair with different bases are investigated through thermal melting (T-m) experiments on the resulting DNA duplexes. Furthermore, computational models of the imidazole-modified DNAs are found to be in good agreement with the results of the thermal melting experiments.

  DOI：

  10.1055/s-0034-1378451
• 作为产物：
  描述：

  1-O-benzoyl-3,5-di-O-benzyl-2-deoxy-D-ribofuranose 在 四丁基二氟三苯硅酸铵 作用下， 以 二氯甲烷 为溶剂， 生成 3,5-di-O-benzyl-2-deoxy-β-D-ribofuranosyl cyanide
  参考文献：
  名称：

  Stereoselective Construction of 1β-Azide- and 1β-Cyano-2-deoxyribose Derivatives

  摘要：

  A new method has been developed for the beta-selective introduction of azido and cyano groups at the anomeric position of 2-deoxyribose derivatives. This method proceeds via the formation of a collidinium salt intermediate and allows for the stereoselective construction of 1 beta-azido- and 1 beta-cyano-2-deoxy-D-ribose derivatives. 2-Deoxy-D-ribose compounds bearing an acetoxy or tert-butoxycarbonyloxy group at their anomeric position performed well as starting materials for the formation of the corresponding 1 beta-azide and 1 beta-cyanide derivatives, respectively. H-1 NMR studies of the salt intermediates revealed that the nucleophilic substitution reaction of the salt intermediates proceeded in a S(N)2-fashion.

  DOI：

  10.3987/com-14-s(k)86

文献信息

• Highly stereoselective synthesis of aryl/heteroaryl-<i>C</i>-nucleosides <i>via</i> the merger of photoredox and nickel catalysis
  作者：Yingying Ma、Shihui Liu、Yifan Xi、Hongrui Li、Kai Yang、Zhihao Cheng、Wei Wang、Yongqiang Zhang

  DOI：10.1039/c9cc07184a

  日期：——

  developed. The reaction proceeds smoothly under visible-light irradiation and features the using of cost-effective and easily handled catalysts and starting materials, which allows the highly stereoselective synthesis of diverse aryl/heteroaryl-C-nucleosides in moderate to high yields.

  已经开发了异核糖基/脱氧核糖基酸与芳基/杂芳基溴化物的光氧化还原/镍双催化的脱羧交叉偶联反应。该反应在可见光照射下可顺利进行，其特点是使用经济高效且易于操作的催化剂和起始原料，从而可以以中等至高收率高度立体选择性地合成各种芳基/杂芳基-C-核苷。
• Synthese neuer Pyridin-, Pyrindin- bzw. Isochinolin-substituierter α- und β-C-Nukleoside der 2-Desoxy-D-ribose / Synthesis of Novel Pyridine-, Pyrindine- and Isoquinoline-Substituted α- and β-C-Nucleosides of 2-Deoxy-D-ribose
  作者：Gunther Seitz、Jens Lachmann

  DOI：10.1515/znb-1999-0420

  日期：1999.4.1

  of 2-deoxy-α- and -β-D-ribose 8 and 9 have been synthesized and successfully transformed to the protected 1,2,4-triazine-C -nucleosides 11 and 12 using an inverse type Diels-Alder reaction with the 1,2,4,5-tetrazine 10. The electron deficient diazadiene system of both C -nucleosides 11 and 12 proved to be highly reactive in a consecutive [4 + 2] cycloaddition with inverse electron demand towards several

  已经合成了 2-脱氧-α-和-β-D-核糖 8 和 9 的新型亚氨基酯，并使用反型 Diels-成功转化为受保护的 1,2,4-三嗪-C-核苷 11 和 12。与 1,2,4,5-四嗪 10 的 Alder 反应。 C-核苷 11 和 12 的缺电子二氮杂二烯系统在连续的 [4 + 2] 环加成反应中被证明是高度反应性的，对几个富电子的电子需求相反亲二烯体在成功脱保护后产生新型吡啶-、吡啶-和异喹啉-C-核苷 2-脱氧-α-D-核糖的 15、18 和 21 和 2-脱氧-β-D-核糖的 23、25 和 27。
• Synthesis of novel C-nucleosides with potential applications in combinatorial and parallel synthesis
  作者：Robert M Adlington、Jack E Baldwin、Gareth J Pritchard、Keith C Spencer

  DOI：10.1016/s0040-4039(99)02078-x

  日期：2000.1

  di-substituted pyrimidinyl C-nucleosides have been synthesised using a flexible synthetic methodology. This methodology conveniently allows the synthesis of alpha and beta nucleosides, both of which are of biological interest. Reactive acetylenic ketones, derived from 2-deoxyribose, can be reacted with substituted amidines to give new families of C-nucleoside natural product analogues.

  已经使用灵活的合成方法合成了新型的二取代的嘧啶基C-核苷。该方法方便地允许合成具有生物学意义的α和β核苷。衍生自2-脱氧核糖的反应性炔酮可与取代的am反应，得到新的C-核苷天然产物类似物家族。
• [EN] DEUTERATED CHEMICAL MODIFICATION AND OLIGONUCLEOTIDE INCLUDING SAME<br/>[FR] MODIFICATION CHIMIQUE DEUTÉRÉE ET OLIGONUCLÉOTIDE LA COMPRENANT<br/>[ZH] 氘代化学修饰和包含其的寡核苷酸
  申请人：TUOJIE BIOTECH SHANGHAI CO LTD

  公开号：WO2023208023A1

  公开（公告）日：2023-11-02

  本公开涉及氘代化学修饰和包含其的寡核苷酸。具体而言，本公开涉及一种寡核苷酸，其包含式(I)所示的化学修饰或其互变异构体修饰，其中官能团如本公开中定义。
• 一种核酸配体、其缀合物、制备方法及用途
  申请人：上海拓界生物医药科技有限公司

  公开号：CN114853829A

  公开（公告）日：2022-08-05

  本公开提供了一种核酸配体、其缀合物、制备方法及用途。具体而言，本公开提供一种配体，结构如式(I)所示，本公开提供的配体通过与核酸缀合达到了优异的表达抑制效果。