1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabinofuranose | 57236-69-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabinofuranose
• 英文别名: [(2R,3R,4S)-5-acetyloxy-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 57236-69-8
• 化学式: C₂₈H₂₄O₉
• 分子量: 504.493
• InChiKey: GCZABPLTDYVJMP-KKDYRJFOSA-N

物化性质

• 沸点：
  621.0±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabinofuranose 在 吡啶 、 四丁基氟化铵 、 四氯化锡 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 32.5h， 生成 N⁴-benzoyl-1-[5-O-(dimethoxytrityl)-2-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-β-D-ribofuranosyl]cytosine 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  Oligonucleotides Containing Disaccharide Nucleosides

  摘要：

  Disaccharide nucleosides with 2'-O-(D-arabinofuranosyl), 2'-O-(L-arabinofuranosyl), 2'-O-(D-ribopyranosyl), 2'-O-(D-erythrofuranosyl), and 2'-O-(5-azido-5-deoxy-D-ribofuranosyl) substituents were synthesized. These modified nucleosides were incorporated into oligonucleotides (see Table). Single substitution resulted in a DeltaT(m) of +0.5 to -1.4 degrees for DNA/RNA and a DeltaT(m) of - 0.8 to -4.7 degrees for DNA/DNA duplexes. These disaccharide nucleosides can be well accommodated in RNA/DNA duplexes, and the presence of a NH2- C(5") group has a beneficial effect on duplex stability.

  DOI：

  10.1002/1522-2675(20010815)84:8<2387::aid-hlca2387>3.0.co;2-f
• 作为产物：
  描述：

  D-arabinofuranose 在 吡啶 、 硫酸 、 溶剂黄146 、 乙酰氯 作用下， 反应 6.0h， 生成 1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabinofuranose
  参考文献：
  名称：

  A One-Pot Synthesis of 1-α- And 1-β-D-Arabinofuranosyl-2-Nitroimidazoles: Synthons to the Markers of Tumor Hypoxia

  摘要：

  1-alpha- and 1-beta-D-Arabinofuranosyl-2-nitroimidazole (alpha-AZA and beta-AZ A) are synthons for a number of potential markers of tissue hypoxia. A one pot synthesis in which 2-nitroimidazole is coupled with a mixture of alpha-and beta-1-O-acetyl-2-3,5-tri-O-benzoyl-D-arabinofuranose in the presence of stannic chloride, followed by deprotection using ammonia/methanol, is described. Previously reported conditions for coupling 2-nitroimidazole to 1-alpha-bromoarabinofuranose protected by base-hydrolyzable groups afforded alpha-AZA almost exclusively.

  DOI：

  10.1081/ncn-200055700

文献信息

• [EN] MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS OLIGOMÈRES MODIFIÉS ET LEURS UTILISATIONS
  申请人：IONIS PHARMACEUTICALS INC

  公开号：WO2021030763A1

  公开（公告）日：2021-02-18

  The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.

  本公开提供了包含至少一种立体非标准核苷酸的修饰寡核苷酸的寡聚化合物。包括由12-30个连接的核苷酸组成的修饰寡核苷酸的寡聚化合物，其中修饰寡核苷酸的至少一个核苷酸是立体非标准核苷酸；且所述寡聚化合物选自RNAi化合物、修饰CRISPR化合物和人工mRNA化合物。
• Fused pyrimidines.<b>7</b>. Nucleosides of pyrimidopyrimidinediones and pteridinediones as potential chemotherapeutic agents
  作者：A. Nagarajan、Bernard R. Meltsner、Thomas J. Delia

  DOI：10.1002/jhet.5570340532

  日期：1997.9

  Several nucleoside derivatives of pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione 1 and 2,41H,3H-pteridinedione 2 were prepared. Treating the appropriate silylated nucleobase with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofura-nose 3 in the presence of trimethylsilyl Inflate gave 4 and 8 which, upon debenzoylation, gave 5 and 9, respectively. Treatment of 4 with phosphorus pentasulfide afforded the sulfur

  嘧啶的几个核苷衍生物[4,5- d ]嘧啶-2,4（1 ħ，3 ħ） -二酮1和2,4- 1 ħ，3 ħ -pteridinedione 2制备。在三甲基甲硅烷基膨胀酸酯的存在下，用1 - O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-核呋喃糖-鼻子3处理适当的甲硅烷基化的核碱基，得到4和8，在脱苯甲酰化后，得到5和分别为9。用五硫化二磷处理4得到硫取代的化合物6。同样，脱保护得到7。通过用甲硅烷基化的核碱基处理1- O-乙酰基-2,3,5-三-O-苯甲酰基-D-阿拉伯呋喃糖10得到阿拉伯糖衍生物，得到11和13。脱苯甲酰化分别得到游离的阿拉伯核苷12和14。脱氧衍生物16是通过1与1-氯-3，5-二-O-乙酰基-2-脱氧-D-呋喃呋喃糖15反应制备的。用甲醇氨将16脱乙酰，得到α-端基异构体17。
• A Procedure for Facile Synthesis of Nucleosides Using N, O-Bistrimethylsilylacetamide in the Presence of Natural Phosphate Coated with Potassium Iodide
  作者：Laila Baddi、Michael Smietana、Said Sebti、Jean-Jacques Vasseur、Hassan B. Lazrek

  DOI：10.2174/157017810791112441

  日期：2010.4.1

  yields under mild conditions by N-glycosylation of 1-O-acetyl D/L- arabino, and xylofuranose, with silylated nucleobases (uracil, thymine and 6- azauracil) in acetonitrile using natural phosphate (NP) coated with potassium iodide in BSA as catalyst.

  通过1-O-乙酰基D / L-阿拉伯糖和木呋喃糖的N-糖基化和甲硅烷基化的核碱基（尿嘧啶，胸腺嘧啶）在温和条件下以高收率合成了几种α-D/ L-阿拉伯糖苷和β-D/ L-木糖苷使用在BSA中用碘化钾包被的天然磷酸盐（NP）作为催化剂，在乙腈中加入6-氮杂尿嘧啶和6-氮杂嘧啶）。
• Janus glycosides of next generation: Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides
  作者：Elena V. Stepanova、Polina I. Abronina、Alexander I. Zinin、Alexander O. Chizhov、Leonid O. Kononov

  DOI：10.1016/j.carres.2018.11.013

  日期：2019.1

  preparative synthesis of per-O-acyl derivatives of 4-(3-chloropropoxy)phenyl (CPP) glycosides of a series of common mono- and disaccharides (d-glucose, d-galactose, d-mannose, l-rhamnose, d-arabinofuranose, d-glucosamine, lactose) are described. The CPP glycosides obtained were transformed in almost quantitative yields to the corresponding unprotected 4-(3-azidopropoxy)phenyl (APP) glycosides, which could

  高效合成一系列常见单糖和二糖（d-葡萄糖，d-半乳糖，d-甘露糖，l-描述了鼠李糖，d-阿拉伯呋喃糖，d-葡萄糖胺，乳糖。将获得的CPP糖苷以几乎定量的产率转化为相应的未保护的4-（3-叠氮基丙氧基）苯基（APP）糖苷，这些糖苷可能成为具有可裂解间隔子糖苷配基的下一代Janus糖苷，可用于缀合或进一步转化。
• Silver-assisted gold-catalyzed solid phase synthesis of linear and branched oligosaccharides
  作者：Yogesh Sutar、Madhuri Vangala、Srinivas Hotha

  DOI：10.1039/d1cc06270k

  日期：——

  Unlike solid phase synthesis of peptides, synthesis of oligosaccharides by solid phase methods is lagging behind owing to inherent challenges faced while executing glycosidations. In this communication, silver-assisted gold-catalyzed glycosidations are found to be excellent for solid phase oligosaccharide synthesis. Glycosidations under catalytic conditions, one time coupling with four equivalents

  与肽的固相合成不同，由于在进行糖苷化时面临固有的挑战，通过固相方法合成寡糖处于滞后状态。在这篇通讯中，发现银辅助金催化的糖苷化对于固相寡糖合成非常有效。催化条件下的糖苷化、与四当量供体的一次偶联、25°C 下不到 30 分钟的反应以及甲硅烷基和苯甲酸酯保护基团的树脂脱保护是其显着特征。光裂解聚糖具有受保护的氨基官能团，可用于生物共轭。该方法的多功能性是通过合成线性和支化呋喃五阿拉伯糖苷而建立的。