5-O-tert-butyldimethylsilyl-1,4-anhydro-2-deoxy-D-erythro-pentitol | 194724-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 5-O-tert-butyldimethylsilyl-1,4-anhydro-2-deoxy-D-erythro-pentitol
• 英文别名: (2R,3S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]tetrahydrofuran-3-ol；(2R,3S)-2-(((Tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-3-OL；(2R,3S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-ol
• CAS: 194724-12-4
• 化学式: C₁₁H₂₄O₃Si
• 分子量: 232.395
• InChiKey: SEZAYGJHXCJLIM-VHSXEESVSA-N

物化性质

• 沸点：
  277.6±20.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-O-tert-butyldimethylsilyl-1,4-anhydro-2-deoxy-D-erythro-pentitol 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-D-ribose
  参考文献：
  名称：

  Synthesis of 1,4-Anhydro-2-deoxy-D-ribitol Derivatives from Thymidine

  摘要：

  1,2-Dideoxyribose 5-O-succinate, a component of solid support employed in the synthesis of ribozymes, was synthesized from thymidine. The key step was elimination of nucleobase from 2 to afford glycal 3. A number of catalysts for this reaction were tested, resulting in improved and scaleable synthesis. Hydrogenation of the resulting glycal afforded 1,2-dideoxyribose derivative 4 in a high yield.

  DOI：

  10.1081/ncn-120022952
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 palladium on activated charcoal 甲烷磺酸 、 氢气 、 三氟乙酸吡啶 作用下， 以 甲醇 为溶剂， 20.0~140.0 ℃ 、206.84 kPa 条件下， 反应 6.75h， 生成 5-O-tert-butyldimethylsilyl-1,4-anhydro-2-deoxy-D-erythro-pentitol
  参考文献：
  名称：

  使用改进的呋喃糖醇制备方法从胸苷合成 1,4-Anhydro-2-deoxy-d-ribitol 衍生物

  摘要：

  已经研究了通过从胸苷中消除核碱基来制备呋喃糖苷。对该反应的许多催化剂进行了测试，从而产生了改进的和可规模化的合成。所得糖醛的氢化以高产率提供了5-保护的1,4-脱水-2-脱氧-D-核糖醇衍生物。

  DOI：

  10.1055/s-2002-33639

文献信息

• [EN] HYDROXAMATE COMPOUNDS AS ANTAGONISTS OF THE ADENOSINE A2A RECEPTOR<br/>[FR] COMPOSÉS HYDROXAMATE EN TANT QU'ANTAGONISTES DU RÉCEPTEUR A2A DE L'ADÉNOSINE
  申请人：ADORX THERAPEUTICS LTD

  公开号：WO2020260857A1

  公开（公告）日：2020-12-30

  The present invention relates to compounds of formula I shown below: (I) wherein R1, R2 and R3 are each as defined in the application. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of diseases or conditions in which adenosine A2a receptor activity is implicated, such as, for example, cancer.

  本发明涉及下面所示的式I的化合物：(I)，其中R1、R2和R3在申请中各自定义。本发明还涉及制备这些化合物的方法，包括含有它们的药物组合物，以及它们在治疗腺苷A2a受体活性参与的疾病或症状中的用途，例如癌症。
• Photo Amidoglycosylation of an Allal Azidoformate. Synthesis of <i>β</i>-2-Amido Allopyranosides
  作者：Cindy Kan、Charli M. Long、Moushumi Paul、Christina M. Ring、Sarah E. Tully、Christian M. Rojas

  DOI：10.1021/ol0069002

  日期：2001.2.1

  azidoformate provoked intramolecular nitrene insertion into the glycal C=C unit and allowed direct incorporation of alcohol nucleophiles as beta-disposed substituents at C-1. The 2-amido allopyranoside products were elaborated via N-acylation and selective oxazolidinone hydrolysis, providing N-Boc-protected 2-amino sugars and simplifying stereochemical assignments. Synthesis of the potentially labile allal

  [图：见正文] C-3叠氮基甲酸酯的光解引发了分子内腈插入到糖基C = C单元中，并允许醇亲核体作为β取代基直接掺入C-1。通过N-酰化和选择性恶唑烷酮水解工艺精制了2-酰胺基别洛吡喃糖苷产品，提供了N-Boc保护的2-氨基糖，并简化了立体化学分配。通过使相应的羰基咪唑啉化物与三甲基甲硅烷基叠氮化物在二丁基氧化锡的促进下反应，可以实现潜在不稳定的脲基叠氮甲酸酯的合成。
• Amidoglycosylation via Metal-Catalyzed Internal Nitrogen Atom Delivery
  作者：Elana Levites-Agababa、Elnaz Menhaji、Lisa N. Perlson、Christian M. Rojas

  DOI：10.1021/ol025634k

  日期：2002.3.1

  [reaction: see text] Rhodium and copper acyl nitrenoids are likely intermediates in amidoglycosylation reactions of allal 3-carbamates. Iodine(III)-mediated nitrenoid formation, interaction of this species with the glycal enol ether pi-system, and highly beta-stereoselective glycosylation occur in a one-pot process that requires no additional Lewis acid activation.

  [反应：见正文]铑和铜的酰基亚硝基化合物可能是3-氨基甲酸酯的酰胺基糖基化反应的中间体。碘（III）介导的类固醇形成，该物质与糖基烯醇醚pi系统的相互作用以及高度β-立体选择性的糖基化都可以通过一锅法完成，无需额外的路易斯酸活化。
• Iron(II)-promoted amidoglycosylation and amidochlorination of an allal C3–azidoformate
  作者：David G. Churchill、Christian M. Rojas

  DOI：10.1016/s0040-4039(02)01658-1

  日期：2002.9

  Iron(II) halides promoted intramolecular alkene amidation in a C3-allal azidoformate. In the presence of alcohols, one-pot beta-glycosylation followed. Without added alcohol, amidochlorination occurred using FeCl2, providing an anomeric mixture of glycosyl chlorides which could be used in subsequent silver ion-mediated couplings. A 2-amido glycosyl chloride with a nitrogen-bound iron center is proposed as the glycosylating agent for the in situ amidoglycosylations with FeCl2. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of bis-abasic cyclic dinucleotide, bis-(3→5)-cyclic Bis(1,4-anhydro-2-deoxy-d-erythro-pentitol-3-phosphate), an inhibitor HIV-1 integrase
  作者：H.Keith Chenault、Robert F. Mandes

  DOI：10.1016/s0040-4020(97)00363-3

  日期：1997.8

  Bis-abasic cyclic dinucleotide, bis-(3-->5)-cyclic bis(1,4-anhydro-2-deoxy-D-erythro-pentitol-3-phosphate) (1), was prepared from 2-deoxy-D-ribose in nine convergent steps, in 18% overall yield. (C) 1997 Elsevier Science Ltd.