6-acetylamino-9-[(2,3-di-O-acetyl)-β-D-ribofuranosyl]purine | 80444-51-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-acetylamino-9-[(2,3-di-O-acetyl)-β-D-ribofuranosyl]purine
• 英文别名: N²-acetyl-2α,3α-O-diacetyl-deoxyguanosine；N⁴-acetyl-2',3'-di-O-acetyladenosine；2',3'-O-6-N-triacetyladenosine；N6-Ac-2',3'-OAc-adenosine；N⁶,O^2'_,O3'-triacetyl-adenosine；2',3'-Di-O-acetyl-6-N-acetyl-tubercidin；[(2R,3R,4R,5R)-5-(6-acetamidopurin-9-yl)-4-acetyloxy-2-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 80444-51-5
• 化学式: C₁₆H₁₉N₅O₇
• 分子量: 393.356
• InChiKey: YRYKJGDNRJUHEA-XNIJJKJLSA-N

物化性质

• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-acetylamino-9-[(2,3-di-O-acetyl)-β-D-ribofuranosyl]purine 在 四氧化锇 、 三氟化硼乙醚 、 双氧水 作用下， 以 四氢呋喃 、 丙酮 、 叔丁醇 为溶剂， 生成 4'',6''-di-O-acetyl-α-D-mannopyranosyl-(1->5)-2',3'-di-O-acetyl-N⁶-acetyladenosine
  参考文献：
  名称：

  Syntheses of 5′-O-glycosylnucleosides

  摘要：

  A general synthetic approach to 2,3-unsaturated glycosides connecting with nucleosides involving Ferrier rearrangements of glycals is discussed. The new compounds were identified by NMR and MS (HRFAB(+)). The hydroxylation of the resulting 2,3-unsaturated glycosides was completed using OsO4 to give 5'-O-glycosylnucleosides in good yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00214-1
• 作为产物：
  描述：

  N⁶,O^2',O^3'-triacetyl-[5']adenylic acid 生成 6-acetylamino-9-[(2,3-di-O-acetyl)-β-D-ribofuranosyl]purine
  参考文献：
  名称：

  MITROFANOV, E. V.;KAVUNENKO, A. P.;PYAJVINEN, EH. A.;KRASNOPEVTSEVA, M. G+

  摘要：

  DOI：

文献信息

• Reliable Synthesis of Various Nucleoside Diphosphate Glycopyranoses
  作者：Saskia Wolf、Tanja Zismann、Nathalie Lunau、Chris Meier

  DOI：10.1002/chem.200900572

  日期：2009.8.3

  A reliable and high yielding synthetic pathway for the synthesis of the biologically highly important class of nucleoside diphosphate sugars (NDP‐sugars) was developed by using various cycloSal‐nucleotides 1 and 9 as active ester building blocks. The reaction with anomerically pure pyranosyl‐1‐phosphates 2 led to the target NDP‐sugars 20–45 in a nucleophilic displacement reaction, which cleaves the

  通过使用各种环Sal-核苷酸1和9作为活性酯结构单元，开发了一种可靠且高产的合成途径，用于合成生物学上非常重要的一类核苷二磷酸糖（NDP-糖）。与端基异构体纯的吡喃糖基-1-磷酸的反应2导致目标NDP-糖20 - 45在亲核取代反应，其切割的环在端基异构体纯的形式萨尔部分。作为核苷，可使用胞苷，尿苷，胸苷，腺苷，2'-脱氧鸟苷和2'，3'-二脱氧-2'，3'-二脱氢胸苷，而D-葡萄糖，D的磷酸盐引入了半乳糖，D-甘露糖，D - N-氨基葡萄糖，D - N-半乳糖胺，D-岩藻糖，L-岩藻糖以及6-脱氧-D-果糖。
• Synthesis of Nucleoside Di- and Triphosphates and Dinucleoside Polyphosphates with <i>cyclo</i>Sal-Nucleotides
  作者：Svenja Warnecke、Chris Meier

  DOI：10.1021/jo802348h

  日期：2009.4.17

  A new and efficient method for the synthesis of nucleoside di- and triphosphates as well as dinucleoside polyphosphates (NpnN′) is described. 5-Acceptor-substituted (5-nitro and 5-chloro) cycloSal-nucleotides are used as starting material that were reacted with a variety of phosphate nucleophiles as pyrophosphate or nucleotides to the corresponding products in short times and very good yields. After

  描述了一种合成核苷二磷酸和三磷酸以及二核苷多磷酸（Np n N'）的新的有效方法。5-受体取代的（5-硝基和5-氯）环Sal核苷酸被用作起始原料，可与各种磷酸盐亲核试剂（如焦磷酸盐或核苷酸）在短时间内以非常高的收率反应成相应的产物。在消耗了起始的环式Sal-磷酸三酯之后，首先将保护基团裂解，最后通过RP柱色谱分离产物。给出了在天然核苷中发现的所有五个嘧啶和嘌呤碱基以及一个非天然嘧啶碱基的实例，以证明该方法可以普遍应用。
• Synthesis and Enzymic Hydrolysis of Acylated Adenosine Derivatives
  作者：Ž. Car、V. Petrović、S. Tomić

  DOI：10.1080/07328300601059284

  日期：2006.12.1

  5‐tri‐O‐pivaloyl)‐β‐D‐ribofuranosyl]purine (5) were subsequently submitted to hydrolysis catalyzed by a number of hydrolytic enzymes. Regioselective enzymic deacetylation at the primary hydroxyl group of 3 and 4 with butyrylcholinesterase (BChE) produced 6‐acetylamino‐9‐[(2,3‐di‐O‐acetyl)‐β‐D‐ribofuranosyl]purine (9) and 6‐amino‐9‐[(2,3‐di‐O‐acetyl‐β‐D‐ribofuranosyl]purine (10), respectively. All structures were established

  摘要通过将腺苷（6-氨基-9-（β-D-核呋喃呋喃糖基）嘌呤（1）与吡啶中不同的乙酸酐和/或新戊酰氯摩尔当量酰化，制得各种腺苷衍生物，化合物6-乙酰氨基-9 ‐ [（（2,3,5-三-O-乙酰基）-β-D-呋喃呋喃糖基]嘌呤（3），6-氨基-9-[（2,3,5-三-O-乙酰基）-β- D-核呋喃糖基]嘌呤（4）和6-新戊酰氨基-9-[（2,3,5-三-O-新戊酰基）-β-D-呋喃核糖基]嘌呤（5）随后被许多催化剂水解丁酰胆碱酯酶（BChE）在3和4的伯羟基上的区域选择性酶促脱乙酰基产生6-乙酰氨基-9-[（2,3-di-O-乙酰基）-β-D-呋喃呋喃糖基]嘌呤（9 ）和6-氨基-9-[（2,3-二-O-乙酰基-β-D-呋喃核糖基]嘌呤（10），所有结构均通过1H和13C NMR光谱确定。
• Synthesis of a Bioreversibly Masked Lipophilic Adenosine Diphosphate Ribose Derivative
  作者：Katharina Pahnke、Chris Meier

  DOI：10.1002/cbic.201700232

  日期：2017.8.17

  Sugar nucleotide delivery systems: Lipophilic ADPR analogues were prepared bearing acetyl protecting groups together with a designed biodegradable group at only one of the phosphate moieties. The compounds showed high stability in PBS (pH 7.3) but enzymatic hydrolysis revealed that the unmasked ADPR was ultimately formed.

  糖核苷酸递送系统：制备亲脂性ADPR类似物，其仅在一个磷酸部分上带有乙酰基保护基以及设计的可生物降解基团。该化合物在PBS（pH 7.3）中显示出高稳定性，但酶促水解表明最终形成了未掩盖的ADPR。
• New Silybin Scaffold for Chemical Diversification: Synthesis of Novel 23-Phosphodiester Silybin Conjugates
  作者：Giovanni Di Fabio、Armando Zarrelli、Valeria Romanucci、Marina Greca、Lorenzo De Napoli、Lucio Previtera

  DOI：10.1055/s-0032-1317688

  日期：——

  Silybin is the major component (ca. 30%) of the silymarin complex extracted from the seeds of Silybum marianum, with multiple biological activities operating at various cell levels. As an ongoing effort toward the exploitation of natural products as scaffolds for chemical diversification at readily accessible positions, we present here an efficient synthetic procedure to obtain new 23-phosphodiester silybin conjugates with different labels. A key point in our approach is the new 3,5,7,20-tetra-O-acetylsilybin-23-phosphoramidite, useful for a variety of derivatizations following a reliable and well-known chemistry. The feasibility of the procedure has been demonstrated by preparing new 23-silybin conjugates, exploiting standard phosphoramidite chemistry.