(2S,3S,4R,5S)-3,4,5-triacetoxytetrahydrofuran-2-carboxylic acid | 1012864-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S,4R,5S)-3,4,5-triacetoxytetrahydrofuran-2-carboxylic acid
• 英文别名: (2S,3S,4R,5S)-3,4,5-triacetyloxyoxolane-2-carboxylic acid
• CAS: 1012864-56-0
• 化学式: C₁₁H₁₄O₉
• 分子量: 290.227
• InChiKey: BFEJWDAKSZKAKR-PKIKSRDPSA-N

物化性质

• 沸点：
  417.5±45.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S)-3,4,5-triacetoxytetrahydrofuran-2-carboxylic acid 在 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 (2S,3S,4R,5R)-methyl 3,4-diacetoxy-5-(6-(3-methylbenzylamino)-2-(5-methylpyridin-3-yl)-9H-purin-9-yl)-tetrahydrofuran-2-ylcarboxylate
  参考文献：
  名称：

  [EN] ADENOSINE A3 RECEPTOR AGONISTS, PREPARATION METHODS AND USES THEREOF
  [FR] AGONISTE RÉCEPTEUR A3 DE L'ADÉNOSINE, PROCÉDÉ DE PRÉPARATION ASSOCIÉ ET UTILISATION ASSOCIÉE
  [ZH] A3腺苷受体激动剂及其制备方法和用途

  摘要：

  公开号：

  WO2022143740A8
• 作为产物：
  描述：

  利巴韦林杂质38 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 16.0h， 生成 (2S,3S,4R,5S)-3,4,5-triacetoxytetrahydrofuran-2-carboxylic acid
  参考文献：
  名称：

  An efficient convergent synthesis of adenosine-5′-N-alkyluronamides

  摘要：

  Herein we report an efficient synthesis of adenosine-5'-N-alkyluronamides in which an enzyme-mediated deacetylation reaction is a key to the selective modification of the 5'-N-position, prior to coupling the ribose and purine components via a microwave-assisted Vorbruggen coupling. This approach provides access to highly functionalised adenosines with 2- and N-6-substitutents, which can be incorporated before or after the ribose-coupling step. In all cases the microwave-assisted Vorbruggen coupling conditions afforded anomerically pure purine ribosides in good to excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.100

文献信息

• Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides
  作者：Richard C. Foitzik、Shane M. Devine、Nicholas E. Hausler、Peter J. Scammells

  DOI：10.1016/j.tet.2009.08.057

  日期：2009.10

  Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5'-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5'-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5'-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of potent A(2A) adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5'-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5'-substitution patterns. (c) 2009 Elsevier Ltd. All rights reserved.