1-(9-Adenyl)-1'-hydroxymethyl-diaethylenglycol | 101568-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1-(9-Adenyl)-1'-hydroxymethyl-diaethylenglycol
• 英文别名: 9-<2-Hydroxy-1-(β.β'-dihydroxy-isopropyloxy)-ethyl>-adenin；2-O-<1-(9-Adenyl)-2-hydroxyethyl>glycerin；2-[1-(6-amino-purin-9-yl)-2-hydroxy-ethoxy]-propane-1,3-diol；1,3-Propanediol, 2-[1-(6-amino-9H-purin-9-yl)-2-hydroxyethoxy]-；2-[1-(6-aminopurin-9-yl)-2-hydroxyethoxy]propane-1,3-diol
• CAS: 101568-85-8
• 化学式: C₁₀H₁₅N₅O₄
• 分子量: 269.26
• InChiKey: BZOVHPRDLVWHRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  adenosine 在 NaIO₄ and NaBH₄ supporting Amberlyst A-27 作用下， 以 水 为溶剂， 以70%的产率得到1-(9-Adenyl)-1'-hydroxymethyl-diaethylenglycol
  参考文献：
  名称：

  One pot solid phase cleavage of alpha-diols to primary alcohols. An attractive route to trihydroxy-nucleosides, antiviral precursors.

  摘要：

  DOI：

  10.1016/s0040-4039(00)94877-9

文献信息

• [EN] METHOD FOR SYNTHESIS OF 2'-ALKYL- OR 2'-ALKENYL- OR 2'-ALKYNYL-4'-FLUORO-ADENOSINE DERIVATIVES AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ POUR LA SYNTHÈSE DE DÉRIVÉS DE 2'-ALKYL- OU 2'-ALCÉNYL- OU 2'-ALCYNYL-4'-FLUOROADÉNOSINE ET INTERMÉDIAIRES CORRESPONDANTS
  申请人：JANSSEN BIOPHARMA INC

  公开号：WO2021140471A1

  公开（公告）日：2021-07-15

  A method of making nucleoside 1, which has a 3-hydrocarbyl-5-fluoro-5-(hydroxy-methyl)tetrahydrofuran-3,4-diol ring system, where hydrocarbyl group R1 is lower alkyl, lower alkenyl, or lower alkynyl and R2 may be an adenine moiety having an exocyclic amino group protected as an imidodicarbonate or as a carbamate. Nucleoside 1 is prepared from an intermediate 4 by adding iodine fluoride across the exocyclic double bond to produce a 5-fluoro-5-iodomethyl derivative 5. The iodine atom is displaced with a carboxylic acid nucleophile in the presence of an oxidizing agent to produce a 5-fluoro-5-(acyloxy)methyl ester derivative 7, where R3 is an acyl group. Ester 7 may be converted into compound 1 by cleavage of the ester.

  制备核苷1的方法，核苷1具有一个3-羟基烷基-5-氟-5-(羟甲基)四氢呋喃-3,4-二醇环系统，其中烃基R1为较低的烷基、较低的烯基或较低的炔基，R2可能是具有外环氨基团被保护为酰胺二碳酸酯或为碳酸酯的腺嘌呤基团。通过在外环双键上加入碘氟化物来从中间体4制备核苷1，以产生一个5-氟-5-碘甲基衍生物5。在氧化剂存在下，碘原子被羧酸亲核试剂取代，产生一个5-氟-5-(酰氧基)甲基酯衍生物7，其中R3是酰基。酯7可以通过酯的裂解转化为化合物1。
• High specificity genome editing using chemically modified guide RNAs
  申请人：Agilent Technologies, Inc.

  公开号：US10767175B2

  公开（公告）日：2020-09-08

  The present invention relates to guide RNAs having chemical modifications and their use in CRISPR-Cas systems. The chemically modified guide RNAs have enhanced specificity for target polynucleotide sequences. The present invention also relates to methods of using chemically modified guide RNAs for cleaving or nicking polynucleotides, and for high specificity genome editing.

  本发明涉及具有化学修饰的引导 RNA 及其在 CRISPR-Cas 系统中的应用。经化学修饰的引导 RNA 对目标多核苷酸序列具有更强的特异性。本发明还涉及使用化学修饰的引导 RNA 来裂解或切割多核苷酸以及进行高特异性基因组编辑的方法。
• High Specificity Genome Editing Using Chemically Modified Guide RNAs
  申请人：Agilent Technologies, Inc.

  公开号：US20170355985A1

  公开（公告）日：2017-12-14

  The present invention relates to guide RNAs having chemical modifications and their use in CRISPR-Cas systems. The chemically modified guide RNAs have enhanced specificity for target polynucleotide sequences. The present invention also relates to methods of using chemically modified guide RNAs for cleaving or nicking polynucleotides, and for high specificity genome editing.
• S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS
  申请人：ALIGOS THERAPEUTICS, INC.

  公开号：US20200147124A1

  公开（公告）日：2020-05-14

  Various embodiments provide STOPS™ polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS™ modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS™ modified oligonucleotides, as determined by HBsAg Secretion Assay, is greater than that of a reference compound.
• HBV BINDING OLIGONUCLEOTIDES AND METHODS OF USE
  申请人：Aligos Therapeutics, Inc.

  公开号：US20220056451A1

  公开（公告）日：2022-02-24

  Oligonucleotides that target hepatitis B virus (HBV) viral sequences, such as rcDNA, cccDNA, and HBV transcripts, are described herein. In addition, compositions and kits comprising such oligonucleotides are further described. Further disclosed herein are uses of such oligonucleotides and compositions to reduce rcDNA to cccDNA conversion, reduce cccDNA levels, and/or treat an HBV infection.