3-azido-5-O-benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-3-deoxy-α-D-ribofuranose | 153914-98-8

• 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: 3-azido-5-O-benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-3-deoxy-α-D-ribofuranose
• 英文别名: 3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-1,2-O-isopropyliden-α-D-ribofuranose；3-azido-4-benzoyloxymethyl-5-O-benzoyl-3-deoxy-1,2-O-isopropylidene-α-D-xylofuranose；3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose；3-azido-4-benzoyloxymethyl-5-O-benzoyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose；[(3aR,6S,6aR)-6-azido-5-(benzoyloxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methyl benzoate
• CAS: 153914-98-8
• 化学式: C₂₃H₂₃N₃O₇
• 分子量: 453.452
• InChiKey: ZQKITWFKKHSCCJ-LQWHRVPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-azido-5-O-benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-3-deoxy-α-D-ribofuranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以94%的产率得到3-azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis and evaluation of anti-HIV activity of 3-azido-4-(hydroxymethyl)tetrahydrofuran derivatives containing 2-(thymin-1-yl)methyl, 2-(cytosin-1-yl)methyl or 2-(adenin-9-yl)methyl substituents – a new series of AZT analogues

  摘要：

  以甲基 3-叠氮-3-脱氧-2-O,4-C-亚甲基-D-呋喃核苷 13 为关键中间体，合成了三种单环 AZT 类似物 6、7 和 8{含有 2-[(百里香-1-基)甲基]、2-[(胞嘧啶-1-基)甲基]和 2-[(腺嘌呤-9-基)甲基]取代基的 3-叠氮-4-(羟甲基)四氢呋喃衍生物}。事实证明，所有核苷类似物在 MT-4 细胞中都没有抗艾滋病毒活性。

  DOI：

  10.1039/b009109j
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 sodium periodate 、 sodium azide 、 palladium 10% on activated carbon 、 水 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 3-azido-5-O-benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-3-deoxy-α-D-ribofuranose
  参考文献：
  名称：

  [EN] MODIFIED NUCLEOSIDE PHOSPHORAMIDITES
  [FR] PHOSPHORAMIDITES DE NUCLÉOSIDES MODIFIÉS

  摘要：

  本发明公开涉及包含式(I)和式(II)的5'-磷酰胺基核苷单体的化合物和组合物，以及它们的制备和使用方法，其中取代基如所附权利要求中所定义。

  公开号：

  WO2019053659A1

文献信息

• Synthesis and properties of 3′-amino-2′,4′-BNA, a bridged nucleic acid with a N3′→P5′ phosphoramidate linkage
  作者：Satoshi Obika、S.M. Abdur Rahman、Bingbing Song、Mayumi Onoda、Makoto Koizumi、Koji Morita、Takeshi Imanishi

  DOI：10.1016/j.bmc.2008.09.013

  日期：2008.10

  The synthesis and properties of a bridged nucleic acid analogue containing a N3'-->P5' phosphoramidate linkage, 3'-amino-2',4'-BNA, is described. A heterodimer containing a 3'-amino-2',4'-BNA thymine monomer, and thymine and methylcytosine monomers of 3'-amino-2',4'-BNA and their 5'-phosphoramidites, were synthesized efficiently. The dimer and monomers were incorporated into oligonucleotides by conventional

  描述了包含N3'-> P5'氨基磷酸酯键3'-氨基-2'，4'-BNA的桥接核酸类似物的合成和性质。有效地合成了包含3'-氨基-2'，4'-BNA胸腺嘧啶单体以及3'-氨基-2'，4'-BNA的胸腺嘧啶和甲基胞嘧啶单体及其5'-亚磷酰胺的异二聚体。通过常规的3'-> 5'组装和5'-> 3'反向组装亚磷酰胺方案分别将二聚体和单体掺入寡核苷酸。与天然DNA寡核苷酸相比，含有3'-氨基-2'，4'-BNA残基的修饰寡核苷酸与单链DNA（ssDNA），单链RNA（ssRNA）和双链DNA形成高度稳定的双链体和三链体。链DNA（dsDNA）靶标，相对于ssDNA，ssRNA和dsDNA的平均解链温度（T（m））分别为+2.7到+4.0摄氏度，+ 5.0到+7.0摄氏度和+5.0到+11.0摄氏度。这些增加与2'，4'-BNA修饰的寡核苷酸观察到的增加相当。此外，用单个3'-氨基-2'，4'-BNA
• Synthesis and evaluation of anti-HIV-1 activity of 3′-azido-3′-deoxy-2′-O,4′-C-methylene-linked bicyclic thymine nucleosides
  作者：Anne G. Olsen、Vivek K. Rajwanshi、Claus Nielsen、Jesper Wengel

  DOI：10.1039/b005469k

  日期：——

  4′-C-methylene-linked bicyclic furanose moiety, are synthesized via the 3′-azido-3′-deoxy-4′-C-hydroxymethyl nucleoside 16. The β-D-ribo-configured derivative 4 is shown by NOE experiments to exist in a north-type (3E, C3′-endo) conformation and the α-L-xylo-configured derivative 5 in a south-type (3E, C3′-exo) conformation. Both nucleosides were devoid of anti-HIV activity in MT-4 cells.

  通过3'-叠氮基-3'-脱氧-4'- C-羟甲基合成两个构象锁定的AZT类似物4和5，每个类似物均含有2'- O，4' - C-亚甲基连接的双环呋喃糖部分。核苷16。所述β- d -核糖-构型衍生物4由NOE实验示于北-型存在（3 é，C3'-内）构象，并且α-大号-木糖-构型衍生物5在南型（3 E，C3'-外切）的构象。两个都核苷 在MT-4细胞中没有抗HIV活性。
• Synthesis of a conformationally locked AZT analogue, 3′-azido-3′-deoxy-2′-O,4′-C-methylene-5-methyluridine
  作者：Satoshi Obika、Jun-ichi Andoh、Tomomi Sugimoto、Kazuyuki Miyashita、Takeshi Imanishi

  DOI：10.1016/s0040-4039(99)01324-6

  日期：1999.8

  A bicyclic 3′-azido-3′-deoxythymidine (AZT) analogue with a locked N-conformation, 3′-azido-3′-deoxy-2′-O,4′-C-methylene-5-methyluridine (1a), and its 3′-amino derivative, 3′-amino-3′-deoxy-2′-O,4′-C-methylene-5-methyluridine (1b), were successfully synthesized from D-glucose. The conformation of 1a was also discussed by means of 1H NMR measurements and a molecular modeling (PM3) study.

  具有锁定N构象的双环3'-叠氮基3'-脱氧胸苷（AZT）类似物3'-叠氮基3'-脱氧-2'- O，4' - C-亚甲基-5-甲基尿苷（1a）由D-葡萄糖成功合成了其3'-氨基衍生物3'-氨基-3'-脱氧-2'- O，4' - C-亚甲基-5-甲基尿苷（1b）。还通过1 H NMR测量和分子模型（PM3）研究讨论了1a的构象。
• NOVEL BICYCLONUCLEOSIDE ANALOGUES
  申请人：Sankyo Company, Limited

  公开号：EP1201678B1

  公开（公告）日：2004-09-22
• Novel 4′-Branched Nucleosides
  作者：S. A. Surzhykov、A. A. Krayevsky

  DOI：10.1080/15257779408013221

  日期：1994.12

  Total chemical synthesis of 4'-hydroxymethylnucleosides with an additional modification in a sugar residue was developed. The synthesis was made by condensation of corresponding protected sugars and nucleic bases with subsequent deprotection. In such a way 3'-azido- and 3'-amino-3'deoxy-4'-hydroxymethylribonucleosides, 2',3'-anhydroribo- and 2',3'-anhydrolyxo-4'-hydroxymethylribonucleosides as well as 3'-deoxy-4'hydroxymethylribollucleosides were prepared. At concentrations up to 100 mu M none of them inhibited reproduction of human immunodeficiency virus type 1 in H9 and PBL cells as well as human herpes simplex virus type 2 and human cytomegalovirus in vero cells.