(3S,4S)-1-O-<(1,1-Dimethylethyl)dimethylsilyl>-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-en-2-one | 154976-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S)-1-O-<(1,1-Dimethylethyl)dimethylsilyl>-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-en-2-one
• 英文别名: (3S,4S)-1-tert-butyldimethylsilyloxy-3,4-isopropylidenedioxy-6-methyl-5-heptene-2-one；(3S,4S)-1-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-en-2-one；2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5S)-2,2-dimethyl-5-(2-methylprop-1-enyl)-1,3-dioxolan-4-yl]ethanone
• CAS: 154976-39-3
• 化学式: C₁₇H₃₂O₄Si
• 分子量: 328.524
• InChiKey: FLVLTKINLRJOGW-LSDHHAIUSA-N

物化性质

• 沸点：
  360.2±42.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-1-O-<(1,1-Dimethylethyl)dimethylsilyl>-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-en-2-one 在 ruthenium(IV) oxide 、 sodium periodate 、 lithium aluminium tetrahydride 、 lithium aluminium deuteride 、 二甲基硫 、 臭氧 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 <1'-(2)H>-5-O-<(1,1-Dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-α-D-ribofuranose
  参考文献：
  名称：

  General Approach to the Synthesis of Specifically Deuterium-Labeled Nucleosides

  摘要：

  Starting from D-(-)-ribose, a set of synthetic routes sharing common intermediates has been developed and exemplified in [5'-H-2(2)]-, [4'-H-2]-, [1'-H-2]-, (5'R)-[5'-H-2]-, and (5'S)-[5'-H-2]-N-4-benzoylcytidine and, by deoxygenation, their corresponding 2'-deoxynucleosides. These syntheses provide convenient access to millimolar quantities of deuterium/tritium-labeled natural or unnatural nucleosides for direct use or automated oligonucleotide synthesis.

  DOI：

  10.1021/jo00089a013
• 作为产物：
  描述：

  卡培他滨杂质25 在 4-二甲氨基吡啶 、 硫酸 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,4S)-1-O-<(1,1-Dimethylethyl)dimethylsilyl>-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-en-2-one
  参考文献：
  名称：

  用于研究DNA和RNA的特殊氘代核苷酸的一般合成。

  摘要：

  描述了用于制备在1'，4'或5'位置掺入氘的核糖核苷酸和脱氧核糖核苷酸的有效方法。通过化学合成制备了三种中间体-[1-2H] -D-核糖，[4-2H] -D-核糖和[5-2H（2）]-D-核糖，随后通过以下方法转化为核糖核苷酸和脱氧核糖核苷酸酶促反应。获得毫克量的所需产物，平均氘含量为96 +/- 1％。

  DOI：

  10.1016/s0960-894x(02)00650-9

文献信息

• [EN] SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF<br/>[FR] NUCLÉOSIDES SUBSTITUÉS, NUCLÉOTIDES ET ANALOGUES DE CEUX-CI
  申请人：ALIOS BIOPHARMA INC

  公开号：WO2016100569A1

  公开（公告）日：2016-06-23

  Disclosed herein are nucleosides, nucleotides and nucleotide analogs, methods of synthesizing the same and methods of treating diseases and/or conditions such as a Picornavirus infection with one or more nucleosides, nucleotides and nucleotide analogs.

  本文披露了核苷、核苷酸和核苷酸类似物，其合成方法以及利用一个或多个核苷、核苷酸和核苷酸类似物治疗如小核糖核酸病毒感染等疾病和/或症状的方法。
• Design, synthesis, and antiviral properties of 4′-substituted ribonucleosides as inhibitors of hepatitis C virus replication: The discovery of R1479
  作者：David B. Smith、Joseph A. Martin、Klaus Klumpp、Stewart J. Baker、Peter A. Blomgren、Rene Devos、Caroline Granycome、Julie Hang、Christopher J. Hobbs、Wen-Rong Jiang、Carl Laxton、Sophie Le Pogam、Vincent Leveque、Han Ma、Graham Maile、John H. Merrett、Arkadius Pichota、Keshab Sarma、Mark Smith、Steven Swallow、Julian Symons、David Vesey、Isabel Najera、Nick Cammack

  DOI：10.1016/j.bmcl.2007.02.004

  日期：2007.5

  A series of 4'-substituted ribonucleoside derivatives has been prepared and evaluated for inhibition of hepatitis C virus (HCV) RNA replication in cell culture. The most potent and non-cytotoxic derivative was compound 28 (4'-azidocytidine, R1479) with an IC(50) of 1.28 microM in the HCV replicon system. The triphosphate of compound 28 was prepared and shown to be an inhibitor of RNA synthesis mediated

  制备了一系列的4'-取代核糖核苷衍生物，并评估了其在细胞培养中对丙型肝炎病毒（HCV）RNA复制的抑制作用。最有效和无细胞毒性的衍生物是化合物28（4'-叠氮基吡啶，R1479），在HCV复制子系统中的IC（50）为1.28 microM。制备了化合物28的三磷酸酯，并显示出它是由NS5B（IC（50）= 320 nM）介导的RNA合成抑制剂，NS5B是HCV编码的RNA聚合酶。有关类似物的数据已被用来对这一系列核苷的活性产生一些初步的要求。
• Synthesis of 4′-Trifluoromethyl Nucleoside Analogs
  作者：Janusz Kozak、Carl R. Johnson

  DOI：10.1080/07328319808004312

  日期：1998.12

  A strategy based on the use of (trifluoromethyl)trimethylsilane for introduction of the trifluoromethyl group at the C-4 of ribose has been developed and utilized in the synthesis of various novel 4'-trifluoromethylated nucleoside analogs. Screening of these analogs against HN did not reveal significant biological activity.
• 2′-<i>O</i>-[(4-CF₃-triazol-1-yl)methyl] Uridine – A Sensitive ¹⁹F NMR Sensor for the Detection of RNA Secondary Structures
  作者：Lotta Granqvist、Pasi Virta

  DOI：10.1021/acs.joc.5b00973

  日期：2015.8.21

  A sensitive uridine-derived sensor (viz., 2'-O-[(4-CF3-triazol-1-yOmethyl]uridine, 1) for F-19 NMR spectroscopic monitoring of RNA secondary structures is described. The applicability of 1 is demonstrated by monitoring the thermal denaturation of the following double and triple helical RNA models: (1) a miR 215 hairpin, (2) a poly U-A*U triple helix RNA (bearing two C-G*CH+ interrupts), and (3) a polyadenylated nuclear-nuclear retention element complex. In these RNA models, the F-19 NMR shift of the 2'-O-(CF3-triazolylmethyl) group shows high sensitivity to secondary structural arrangements. Moreover, 1 favors the desired N-conformation, and its effect on both RNA duplex and triplex stabilities is marginal.
• [EN] COMPOUNDS AND METHODS FOR TREATING DISEASE<br/>[FR] COMPOSÉS ET MÉTHODES POUR TRAITER UNE MALADIE
  申请人：[en]ROME THERAPEUTICS, INC.

  公开号：WO2023178133A1

  公开（公告）日：2023-09-21

  The invention provides compounds, compositions and methods for treating medical disorders, such as cancer, an autoimmune disorder, and/or a neurological disorder, and inhibiting LINE1 reverse transcriptase and/or HERV-K reverse transcriptase using a compound according to Formula I or a pharmaceutically acceptable salt thereof, or a related compound provided herein.