6,6-diacetylamino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine | 62420-34-2

• 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: 6,6-diacetylamino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine
• 英文别名: 6-di-N,N-2',3',5'-tri-O-pentaacetyladenosine；N,N-diacetyladenosine triacetate；adenosine pentaacetate；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[6-(diacetylamino)purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 62420-34-2
• 化学式: C₂₀H₂₃N₅O₉
• 分子量: 477.431
• InChiKey: YQSROLADVWODFA-WVSUBDOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6,6-diacetylamino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine 在 potassium cyanide 、 四丁基硝酸铵 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-nitroadenosine
  参考文献：
  名称：

  Regioselective nitration of purine nucleosides: synthesis of 2-nitroadenosine and 2-nitroinosine

  摘要：

  Nitration reactions of 6-substituted purine nucleosides with tetrabutylammonium nitrate/trifluoroacetic anhydride (TBAN/TFAA) have been studied. This nitrating mixture selectively nitrates C-6 substituted purines at the 2-position, but the method is limited to substrates without NH or OH substituents. Acetylated 6-chloropurine riboside was cleanly nitrated (DCM, 0 degrees C, 71%) and converted to nitro substituted adenosine and inosine in a few simple steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02271-6
• 作为产物：
  描述：

  乙酸酐 、 2',3',5'-三乙酰腺苷 在 4-二甲氨基吡啶 作用下， 生成 6,6-diacetylamino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine
  参考文献：
  名称：

  Regioselective nitration of purine nucleosides: synthesis of 2-nitroadenosine and 2-nitroinosine

  摘要：

  Nitration reactions of 6-substituted purine nucleosides with tetrabutylammonium nitrate/trifluoroacetic anhydride (TBAN/TFAA) have been studied. This nitrating mixture selectively nitrates C-6 substituted purines at the 2-position, but the method is limited to substrates without NH or OH substituents. Acetylated 6-chloropurine riboside was cleanly nitrated (DCM, 0 degrees C, 71%) and converted to nitro substituted adenosine and inosine in a few simple steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02271-6

文献信息

• [EN] IMPROVED SYNTHESIS OF 2-SUBSTITUTED ADENOSINES<br/>[FR] SYNTHESE AMELIOREE D'ADENOSINES SUBSTITUEES EN 2
  申请人：CAMBRIDGE BIOTECHNOLOGY LTD

  公开号：WO2005056571A1

  公开（公告）日：2005-06-23

  Synthesis of 2-substituted adenosines of formula (I) using 2-nitro pentabenzoyl adenosine, or 2-nitro pentaacetyl adenosine, as intermediate is described: Formula (I) wherein R = C1-6 alkoxy (straight or branched), a phenoxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C1-6 alkyl, or C1-6 alkoxy), a benzyloxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C1-6 alkyl, or C1-6 alkoxy), or a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-,cyano, nitro, C1-6 alkyl, or C1-6 alkoxy). The methods provide improved yield and purity of product.

  使用2-硝基戊二酰基腺苷或2-硝基戊醋酰基腺苷作为中间体，描述了合成式(I)的2-取代腺苷的方法：式(I)中，R = C1-6烷氧基（直链或支链）、苯氧基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）、苄氧基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）、或苯甲酰基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）。该方法提供了改善产物产量和纯度的效果。
• N6-Acetyl-2′,3′,5′-tri-O-acetyladenosine; A Convenient, ‘Missed Out’ Substrate for Regioselective N6-Alkylations
  作者：Sergey Mikhailov、Vitali Tararov、Svetlana Kolyachkina、Cyril Alexeev

  DOI：10.1055/s-0030-1260090

  日期：2011.8

  A simple and efficient route to N 6-acetyl-2′,3′,5′-tri-O-acetyladenosine (1) was developed based on selective N-deacetylation of pentaacetylated adenosine 2 with methanol at room temperature in the presence of imidazole. Preparative synthesis of 1 was elaborated utilizing a crude mixture of 2 and 1 which is produced by reaction of adenosine with acetic anhydride in pyridine at elevated temperatures

  在咪唑存在下，在室温下用甲醇对五乙酰基腺苷2进行选择性的N-脱乙酰基化反应，建立了一种简单有效的N 6-乙酰基2'，3'，5'- tri - O-乙酰腺苷（1）路线。 。利用2和1的粗混合物，通过腺苷与乙酸酐在吡啶中在升高的温度下反应制备的混合物，详细说明了1的制备合成。从腺苷开始，总产率为1，为80-85％。结果表明1是选择性N 6的便捷底物-烷基化。该研究揭示了在1与活化的烷基卤化物的碱促进反应和1与醇的光延反应中相同的区域选择性。制备了一系列的N 6-烷基腺苷5a - f。通过使用核苷磷酸化酶和碱性磷酸酶的组合对母体核苷衍生物5b，d，e进行酶促转化来制备细胞分裂素6b，d，e。 细胞分裂素-腺苷衍生物-N 6-烷基化-区域选择性-Mitsunobu反应-核苷磷酸化酶
• 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。
• Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹
  作者：Ireneusz Nowak、Martin Conda-Sheridan、Morris J. Robins

  DOI：10.1021/jo051256w

  日期：2005.9.1

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.
• 2-Nitro analogues of adenosine and 1-deazaadenosine: synthesis and binding studies at the adenosine A1, A2A and A3 receptor subtypes
  作者：Martin J. Wanner、Jacobien K. Von Frijtag Drabbe Künzel、Ad P. IJzerman、Gerrit-Jan Koomen

  DOI：10.1016/s0960-894x(00)00415-7

  日期：2000.9

  The influence of nitro substituents on the properties of adenosine and 1-deazaadenosine was studied. Combination of a nitro group at the 2-position with several N-6 substituents such as cyclopentyl and m-iodobenzyl gave a series of analogues with good adenosine receptor affinity, showing directable selectivity for the A(1), A(2A) and A(3) adenosine receptor subtypes. (C) 2000 Elsevier Science Ltd. All rights reserved.