5'-O-trityl-2'-deoxyadenosine | 66503-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-trityl-2'-deoxyadenosine
• 英文别名: O^5'-trityl-2'-deoxy-adenosine；O^5'-Trityl-2'-desoxy-adenosin；(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(trityloxymethyl)oxolan-3-ol
• CAS: 66503-49-9
• 化学式: C₂₉H₂₇N₅O₃
• 分子量: 493.565
• InChiKey: JBKOOOQHHFBZJW-ISJGIBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-O-trityl-2'-deoxyadenosine 在 silica gel 、 三氟乙酸 作用下， 以 甲醇 、 氯仿 为溶剂， 以96%的产率得到2'-脱氧腺苷
  参考文献：
  名称：

  A facile method for deprotection of trityl ethers using column chromatography

  摘要：

  A mild, efficient and inexpensive detritylation method is reported that uses trifluoroacetic acid on a silica gel column to obtain pure, detritylated compounds in one-step. This method is applicable to acid stable as well as acid sensitive compounds with only slight alterations in the procedure. Nineteen examples are given. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01645-8
• 作为产物：
  描述：

  三苯基氯甲烷 、 2'-脱氧腺苷 在 吡啶 作用下， 生成 5'-O-trityl-2'-deoxyadenosine
  参考文献：
  名称：

  Andersen et al., Journal of the Chemical Society, 1954, p. 1882,1884

  摘要：

  DOI：

文献信息

• 2' And 3'-ketonucleosides and their arabino and xylo reduction products
  作者：Fritz Hansske、Danuta Madej、Morris J. Robins

  DOI：10.1016/0040-4020(84)85111-x

  日期：1984.1

  A number of 2',5'- or 3',5'-diprotected ribonucleosides and 5'-protected 2'- or 3'-deoxy-β-D-erythro-pentofuranosyl nucleosides have been oxidized to the corresponding 3' or 2'-ketonucleoside derivatives using chromium trioxide/pyridine/acetic anhydride or dimethyl sulfoxide/ acetic anhydride. Reduction of the carbonyl functions with sodium borohydride gave the inverted arabino, xylo, or deoxy-threo

  许多2'，5'-或3'，5'-双保护核糖核苷和5'-保护的2'-或3'-脱氧-β-D-赤型-戊呋喃糖基核苷已被氧化为相应的3'或2使用三氧化铬/吡啶/乙酸酐或二甲基亚砜/乙酸酐的'-酮核苷衍生物。用硼氢化钠还原羰基官能团，可以通过在糖环的受阻较少的α面上进行攻击，使倒位的阿拉伯糖，木糖或脱氧苏糖异构体成为主要产物。通过证明已经发生了原始羟基的完全氧化，使用硼氢化氘化钠的平行还原证实了差向异构体比率。氘标记还有助于进行NMR 频谱分配。
• Linear free energy relationships and kinetic isotope effects reveal the chemistry of the Ado 2′-OH group
  作者：Mohamed M. Changalov、Dimiter D. Petkov

  DOI：10.1016/j.tetlet.2007.01.139

  日期：2007.3

  Using kinetic isotope effects (KIE) and Hammett correlations, we show that the main role of the adenosine 2′-OH group on deprotonation by the non nucleophilic base DBU during external acyl group transfer is to generate enhanced electron density on the attacking nucleophile through ionization. The small primary KIEs (1.2 and 1.6) and the large Hammett reaction constants (+2.25 and +3.19) obtained for

  使用动力学同位素效应（KIE）和Hammett相关性，我们表明，在外部酰基转移过程中，腺苷2'-OH基团在非亲核碱基DBU的去质子化中的主要作用是通过电离在攻击的亲核试剂上产生增强的电子密度。为2'/ 3'- O - p-取代的苯甲酰基5'- O-三苯甲基腺苷和2'-的乙醇化反应而获得的小一级KIE（1.2和1.6）和大Hammett反应常数（+2.25和+3.19）脱氧腺苷与A N  + D N反应机理一致。根据2'-OH基团在肽键形成的核糖体催化中的化学贡献，讨论了我们结果的含义。
• PROCESS FOR PRODUCING NUCLEIC ACID DERIVATIVES
  申请人：——

  公开号：US20020045744A1

  公开（公告）日：2002-04-18

  There can be provided an excellent industrial process for producing compounds having sugar-moiety hydroxyl groups or halogen atoms reduced in nucleic acids or in derivatives thereof by allowing O-thiocarbonyl derivatives of sugar-moiety hydroxyl groups or allowing halogenated derivatives in the sugar-moiety, in the nucleic acids or in derivatives thereof to react with any one of hypophosphorous acids (including salts thereof) and phosphites (esters) which are inexpensive, non-toxic and safely usable as radical reducing agents in industrial scale, in the presence of a radical reaction initiator. The process of the present invention is an industrially useful and highly safe process for reducing sugar-moiety hydroxyl groups and halogen atoms in nucleic acids or derivatives thereof (including nucleic acid-related compounds) at low costs.

  可以提供一个出色的工业过程，用于通过允许具有糖基羟基或卤原子的化合物在核酸或其衍生物中减少，通过允许糖基羟基的O-硫酰衍生物或在核酸中或其衍生物中允许卤代衍生物与任何一种廉价、无毒且安全可用作工业规模中的自由基还原剂的次磷酸（包括其盐）和磷酸酯（酯）反应，在自由基反应引发剂的存在下。本发明的工艺是一种在低成本下减少核酸或其衍生物（包括核酸相关化合物）中的糖基羟基和卤原子的工业上有用且高度安全的过程。
• Reusable solid-phase supports for oligonucleotides and antisense therapeuticsElectronic supplementary information (ESI) available: CGE data for octathymidine phosphodiester sequences on supports P1–5, P7, P9, and P11–13 PAGE data for phosphorothioate products, dimethoxytrityl analysis and UV measurements on supports P1–7, P9 and P15, step listing for ABI394 DNA synthesizer and CGE and HPLC data for phosporothioate syntheses on support P3. See http://www.rsc.org/suppdata/p1/b1/b105089n/
  作者：Richard T. Pon、Shuyuan Yu、Zhiqiang Guo、Ranjit Deshmukh、Yogesh S. Sanghvi

  DOI：10.1039/b105089n

  日期：2001.10.11

  dGCCCAAGCTGGCATCCGTCA phosphorothioate sequence, on the same synthesis column were performed. A glycerol-CPG synthesis column was satisfactorily used six consecutive times when NH4OH was the cleavage reagent. However, anhydrous NH3 allowed twelve consecutive syntheses without any deterioration in support loading, product quality, or amount of product produced. An improved method for preparing the essential

  已经开发了在可重复使用的固相载体上合成寡核苷酸的通用方法，该方法将大大降低大规模合成的成本。它由五个步骤组成：1，核苷通过Q-连接基（氢醌-O，O）连接到羟基衍生化支持物上'-二乙酸）连接臂; 2，未反应的表面基团的氯乙酰化；3，常规的磷酸二酯或硫代磷酸酯寡核苷酸的合成；4，用含水或无水氨从载体上裂解；和5，用甲醇碳酸钾支持再生。回收过程快速，完全自动化，并且不需要从合成塔中除去载体。用甘油-CPG评估了15种固相支持物，可提供最佳结果。在同一合成柱上连续合成dGCCCAAGAGGGGGCATCCGTCA ISIS 2302。当NH 4 OH作为裂解试剂时，连续六次令人满意地使用甘油-CPG合成柱。但是，无水NH 3允许连续十二次合成，而载体负载，产品质量或产品产量没有任何下降。还描述了一种改进的方法，该方法用于制备Q-接头的必需核苷3'-半胱氨酸，以及硫代磷酸酯DNA相对于磷酸二酯DNA的切割速度出乎意料地慢。
• Process for producing nucleoside derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：EP0999218A1

  公开（公告）日：2000-05-10

  An industrially applicable process is provided for producing nucleic acids or derivatives thereof having their sugar-moiety hydroxyl groups or halogen atoms reduced. According to this process, O-thiocarbonyl derivates of the sugar-moiety hydroxyl groups or derivatives halogenated in the sugar-moiety, are allowed to react, in the presence of a radical reaction initiator, with any one of hypophosphorous acids (including salts thereof) and phosphites (esters) which are inexpensive, non-toxic and safely usable as radical reducing agents on an industrial scale. The process of the present invention is an industrially useful and highly safe process for reducing sugar-moiety hydroxyl groups and halogen atoms in nucleic acids or derivatives thereof (including nucleic acid-related compounds) at low costs.

  本发明提供了一种工业上适用的工艺，用于生产糖分子羟基或卤素原子被还原的核酸或其衍生物。 根据该工艺，糖分子羟基的 O-硫代羰基衍生物或糖分子中卤化的衍生物，在自由基反应引发剂的存在下，可与任何一种次磷酸（包括其盐）和亚磷酸酯（酯）发生反应，次磷酸和亚磷酸酯价格低廉、无毒，可安全地用作工业规模的自由基还原剂。 本发明的工艺是一种工业上有用且高度安全的工艺，可以低成本还原核酸或其衍生物（包括核酸相关化合物）中的糖分子羟基和卤素原子。