5'-deoxy-2',3'-O-isopropylidene-5'-O-methanesulfonyl-uridine | 15083-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5'-deoxy-2',3'-O-isopropylidene-5'-O-methanesulfonyl-uridine
• 英文别名: 5'-O-mesyl-2',3'-isopropylideneuridine；2',3'-O-Isopropyliden-5-O-mesyl-uridin；O^{2'_,O3'_{-isopropylidene-O}5'}-methanesulfonyl-uridine；[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl methanesulfonate
• CAS: 15083-09-7
• 化学式: C₁₃H₁₈N₂O₈S
• 分子量: 362.361
• InChiKey: UPDXJUVQOLRFDB-QCNRFFRDSA-N

物化性质

• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-deoxy-2',3'-O-isopropylidene-5'-O-methanesulfonyl-uridine 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以70%的产率得到5'-azido-5'-deoxy-2',3'-O-isopropylideneuridine
  参考文献：
  名称：

  Copper catalyzed 1,3-dipolar cycloaddition reaction of azides with N-(2-trifluoroacetylaryl)propargylamines

  摘要：

  The synthesis of N-(2-trifluoroacetylaryl)propargylamines 10-14 and 17 is presented. The copper(I) catalyzed cycloaddition reaction of these propargylamines (dipolarophiles) with a series of azides (1,3-dipoles) 18-20, 21 and 24 was found to proceed smoothly in dimethylsulfoxide at room temperature, to furnish the corresponding 1,4-disubstituted-[1,2,3]triazole derivatives 26-36 in moderate to good yields. (c) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.05.015
• 作为产物：
  描述：

  2’,3’邻异亚丙基尿苷 、 甲基磺酰氯 在 吡啶 作用下， 以80%的产率得到5'-deoxy-2',3'-O-isopropylidene-5'-O-methanesulfonyl-uridine
  参考文献：
  名称：

  使用基于芳基碲化物自由基交换过程的分子内自由基环化合成5'，8-环嘌呤和5'，6-环二氢嘧啶核苷。

  摘要：

  C-环嘌呤和C-环二氢嘧啶核苷的合成已使用5'-芳基tellurourosidesides进行。通过N-羟基-2-硫代吡啶酮的乙酰基衍生物的光解反应生成甲基自由基，可以通过自由基交换形成5'-核苷自由基，并以令人满意的产率进行环化。

  DOI：

  10.1016/s0040-4020(01)80885-1

文献信息

• [EN] N4-HYDROXYCYTIDINE AND DERIVATIVES AND ANTI-VIRAL USES RELATED THERETO<br/>[FR] N4-HYDROXYCYTIDINE, SES DÉRIVÉS ET UTILISATIONS ANTI-VIRALES
  申请人：UNIV EMORY

  公开号：WO2016106050A1

  公开（公告）日：2016-06-30

  This disclosure relates to N4-hydroxycytidine derivatives, compositions, and methods related thereto. In certain embodiments, the disclosure relates to the treatment and prophylaxis of viral infections.

  这项披露涉及N4-羟基胞嘧啶衍生物、组合物以及相关方法。在某些实施方式中，该披露涉及治疗和预防病毒感染。
• Synthesis of asymmetrically substituted cyclen-based ligands for the controlled sensitisation of lanthanides
  作者：K. Eszter Borbas、James I. Bruce

  DOI：10.1039/b705757a

  日期：——

  A series of unsymmetrical cyclen-based ligands incorporating an antenna and a quencher have been prepared for the complexation of the visible- (Eu, Tb) and near IR-emitting (Nd, Yb) lanthanides. Eu and Tb were sensitised with coumarin 2, and Nd and Yb with rhodamine. Both antennae were paired with nucleoside (uridine and adenosine) quenchers. The interaction between the quencher and the antenna can be regulated by the addition of the complementary base or DNA to the complexes, resulting in changes in the lanthanide luminescence intensity and lifetime.

  一系列不对称的基于环的配体被制备，以结合可见光（Eu，Tb）和近红外发射（Nd，Yb）的锕系元素。这些配体中，Eu和Tb与香豆素2进行敏化，而Nd和Yb则与罗丹明结合。两个天线都与核苷（尿苷和腺苷）熄灭剂配对。通过向复合物中添加互补碱基或DNA，可以调节熄灭剂与天线之间的相互作用，从而导致锕系元素的发光强度和寿命发生变化。
• シクロペンテン誘導体及びシクロペンテン誘導体の製造方法
  申请人：国立大学法人岐阜大学

  公开号：JP2021070665A

  公开（公告）日：2021-05-06

  【課題】製造工程数が少なくて、単一の立体異性体が得られやすく、高価な触媒や多量の溶媒を必要としないシクロペンテン誘導体及びその製造方法の提供。【解決手段】化学式（ａ）又は（ｂ）で示されるシクロペンテン誘導体（ただし、Xは水酸基の保護基、Bは核酸塩基を示す）、及びフラノース誘導体からの前記シクロペンテン誘導体の製造方法。【選択図】図１

  题目：提供一种制造工程数较少、易得到单一立体异构体、不需要昂贵催化剂或大量溶剂的环戊烯衍生物及其制造方法。 解决方案：提供由化学式（a）或（b）表示的环戊烯衍生物（其中，X是保护基的羟基，B表示核酸盐基），以及从花糖衍生物制造环戊烯衍生物的方法。 选择图：图1。
• Efficient Synthesis of Methylenebis(phosphonate) Analogues of P¹,P²-Disubstituted Pyrophosphates of Biological Interest. A Novel Plausible Mechanism
  作者：Krzysztof W. Pankiewicz、Krystyna Lesiak、Kyoichi A. Watanabe

  DOI：10.1021/ja964058i

  日期：1997.4.1

  Synthesis of novel nucleoside bicyclic trisanhydrides 7 in the reaction of nucleoside-5'-methylenebis-(phosphonate)s (4) with DCC is described. They were obtained by P-1,P-3- and P-2,P-3-dehydration of initially formed P-1,P-2,P-3,P-4-bismethylenetetraphosphonate 6. Reaction of 7 (N = 2',3'-O-isopropylideneadenosin-5'-yl) with 2',3'-O-isopropylidenetiazofurin gave, after hydrolysis and deisopropylidenation, beta-methylene-TAD (10a), the known potent inhibitor of inosine monophosphate dehydrogenase (IMPDH). Similar reaction of 7 with benzyl 2,3-O-isopropylidene-beta-D-riboside followed by hydrolysis and deprotection afforded a new methylenebis(phosphonate) analogue of ADP-ribose 10b. Upon reaction of 7 with riboflavin, the corresponding beta-methylene-FAD (10c) was obtained. Bicyclic trisanhydride 7 prepared from (2',3'-O-isopropylidene-N-4-acetylcytidin-5'yl)methylenebis(phosphonate) was used in the synthesis of the methylenebis(phosphonate) analogues of CDP-ethanolamine 10d and CDP-dipalmitoylglycerol 10e.
• Synthesis of Novel 5′-Uridine-Head Amphiphiles as Model for DNA Molecular Recognition
  作者：Matteo Tiecco、Pietro Di Profio、Raimondo Germani、Gianfranco Savelli

  DOI：10.1080/15257770903306625

  日期：2009.10.28

  Here we describe uridine functionalization in the 5' position, which provides new classes of cationic and nonionic amphiphiles specifically designed. as DNA transfection agents. The Synthetic procedures developed to obtain the cationic uridine-head surfactants prevented intramolecular cyclization. that occurs when. uridine is functionalized in this position without using protecting groups in the uracil.