5'-O-benzoyl-2'-deoxyadenosine | 90362-50-8

• 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: 5'-O-benzoyl-2'-deoxyadenosine
• 英文别名: [(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl benzoate；[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 90362-50-8
• 化学式: C₁₇H₁₇N₅O₄
• 分子量: 355.353
• InChiKey: WTAGHLQWXHCOEV-YNEHKIRRSA-N

物化性质

• 沸点：
  655.2±65.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-benzoyl-2'-deoxyadenosine 在 Barton reagent 、 氨 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2',3'-双脱氧腺苷
  参考文献：
  名称：

  ADA-Bypass by lipophilic cycloSal-ddAMP pro-nucleotides A second example of the efficiency of the cycloSal-Concept

  摘要：

  The synthesis of lipophilic pro-nucleotides of ddAMP 2 based on cycloSal-ddAMP 3a-c is described. Phosphotriesters 3 released ddAMP 2 selectively by a controlled, chemically induced tandem reaction. CycloSal-phosphotriesters 3 exhibited antiviral activity against HIV-1/HIV-2 in CEM cells that where by a factor up to hundred higher as compared to ddA 1. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00265-5
• 作为产物：
  描述：

  2'-脱氧腺苷 生成 5'-O-benzoyl-2'-deoxyadenosine
  参考文献：
  名称：

  LIGUORI, ANGELO;PERRI, ENZO;SINDONA, GIOVANNI;UCCELLA, NICOLA, TETRAHEDRON, 44,(1988) N 1, 229-234

  摘要：

  DOI：

文献信息

• [EN] SOLID-PHASE PURIFICATION OF SYNTHETIC NUCLEIC ACID SEQUENCES<br/>[FR] PURIFICATION EN PHASE SOLIDE DE SÉQUENCES D'ACIDES NUCLÉIQUES SYNTHÉTIQUES
  申请人：US HEALTH

  公开号：WO2018005630A1

  公开（公告）日：2018-01-04

  The invention provides a compound of the formula (I), and a capture support of the formula (9), wherein R1, R2, R3, R6, A, B, D, E, J, K, Q, W, and Z are as defined herein. The invention also provides a method of purifying an oligonucleotide or an oligonucleotide analog composed of "b" nucleotides from a mixture comprising the oligonucleotide or oligonucleotide analog and at least one oligonucleotide or oligonucleotide analog composed of "a" nucleotides, wherein b ≠ a, comprising use of the compound and the capture support.

  该发明提供了一个公式(I)的化合物，以及一个公式(9)的捕获支持物，其中R1、R2、R3、R6、A、B、D、E、J、K、Q、W和Z如本文所定义。该发明还提供了一种从包括寡核苷酸或寡核苷酸类似物和至少一种由"a"核苷酸组成的寡核苷酸或寡核苷酸类似物的混合物中纯化由"b"核苷酸组成的寡核苷酸或寡核苷酸类似物的方法，其中b ≠ a，包括使用该化合物和捕获支持物。
• Protected deoxyadenosines and deoxyguanosines
  申请人：——

  公开号：US20030162957A1

  公开（公告）日：2003-08-28

  Processes are disclosed for the preparation of either an N-acyl deoxyadenosine or an N-acyl deoxyguanosine by acylating the hydroxyl groups and the exocyclic amino group of a corresponding deoxyadenosine or deoxyguanosine with anhydride to form a 3′-, 5′-O-acyl, N-acyl deoxyneucloside and then selectively removing the acyl groups from the hydroxyl groups to form an N-acyl deoxyadenosine or N-acyl deoxyguanosine.

  通过酰化相应的脱氧腺苷或脱氧鸟苷的羟基和外环氨基团，形成3'-、5'-O-酰基、N-酰基脱氧核糖核苷，然后选择性地去除羟基上的酰基，形成N-酰基脱氧腺苷或N-酰基脱氧鸟苷的制备过程已被披露。
• Chemo and regioselective acylation of deoxyribonucleosides by means op n,n-bis-(2-oxo-oxazolidin-3-yl) phosphorodiammidic chloride (bopdc)
  作者：Angelo Liguori、Enzo Perri、Giovanni Sindona、Nicola Uccela

  DOI：10.1016/s0040-4020(01)85111-5

  日期：1988.1

  can be obtained by direct acylation of the substrates with carboxylic acid after activation with N,N-bis-(2-oxo-oxazolidin-3-yl) phosphorodiammidic chloride (BOPDC). In the same experimental conditions a chemoselective benzoylation of unprotected deoxyadenosine can be carried out. Nucleotide building blocks have been prepared from the base labile 5 '-protected nucleosides thus obtained.

  在N，N-双-（2-氧代-恶唑烷-3-基）磷二酰胺基氯化物（BOPDC）活化后，通过用羧酸直接将底物酰化，可获得高产率的5'-酰基-脱氧核糖核苷。在相同的实验条件下，可以进行未保护的脱氧腺苷的化学选择性苯甲酰化。已经从由此获得的碱基不稳定的5'-保护的核苷制备了核苷酸构件。
• C-3' protected monomeric nucleotides and synthesis of oligonucleotides on solid support
  申请人：——

  公开号：US20010044530A1

  公开（公告）日：2001-11-22

  Immobilized nucleotide primers of this invention include a modified nucleotide tethered to a support substrate through a linking group. In particular, the modified nucleotide is constructed such that the C-5′ end of the nucleotide is tetherable to the linking group and the protected C-3′ end is available for further controlled modification, e.g., addition of other nucleotides in specific sequences to the immobilized nucleotide primer. Additionally, the linking group is of sufficient length to allow the immobilized nucleotide primer to be used to synthesize and screen arrays of oligonucleotides, e.g., enzymatic C-3′ primer extension.

  本发明的固定核苷酸引物包括通过连接基团固定在支撑基质上的修饰核苷酸。特别是，修饰核苷酸构建为核苷酸的C-5'末端可连接到连接基团，而受保护的C-3'末端可用于进一步的受控修饰，例如，在固定的核苷酸引物中特定序列的添加其他核苷酸。此外，连接基团的长度足够长，可用于合成和筛选寡核苷酸阵列，例如，酶促C-3'引物延伸。
• Thioether substituted aryl carbonate protecting groups
  申请人：Timar Zoltan

  公开号：US20080146787A1

  公开（公告）日：2008-06-19

  Embodiments of the invention include thioether substituted aryl carbonate protecting groups, and nucleoside monomers protected with thioether substituted aryl carbonate protecting groups. Aspects of the invention further included methods of synthesizing nucleic acids, e.g., oligonucleotides, using such protected nucleoside monomer monomers, as well as nucleic acids produced using methods of the invention and compositions thereof.

  本发明的实施方式包括硫醚取代的芳基碳酸酯保护基，以及使用硫醚取代的芳基碳酸酯保护基保护的核苷单体。本发明的方面还包括使用这种受保护的核苷单体单体合成核酸（例如寡核苷酸）的方法，以及使用本发明的方法合成的核酸及其组成物。