Benzoic acid (2S,5R)-5-methoxy-2,5-dihydro-furan-2-ylmethyl ester | 17081-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (2S,5R)-5-methoxy-2,5-dihydro-furan-2-ylmethyl ester
• 英文别名: [(2S,5R)-5-methoxy-2,5-dihydrofuran-2-yl]methyl benzoate
• CAS: 17081-06-0
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: JWVKELCEMNNZPO-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2S,5R)-5-methoxy-2,5-dihydro-furan-2-ylmethyl ester 在 4-二甲氨基吡啶 、 platinum(IV) oxide 盐酸 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 5-O-benzoyl-1-O-acetyl-2,3-dideoxy-D-glycero-pentofuranose
  参考文献：
  名称：

  Novel dideoxynucleoside isosteres

  摘要：

  Novel 5-aza-7-deaza isosteres of the anti-HIV compounds, dideoxyinosine (ddI) and dideoxyguanosine (ddG), have been prepared by glycosylation of the corresponding isosteric bases with appropriately tailored dideoxyribose components. The glycosylation reactions were regiospecific and the position of glycosylation was established by UV and high-field NMR data. However, attempted preparation of the 3-deaza-5-aza isostere of dideoxyinosine led to a different regioisomer, a ring-extended dideoxycytidine analogue, whose structure was established by X-ray crystallographic data. The 5-aza-7-deaza isosteres of ddI and ddG were more stable with respect to hydrolytic cleavage than ddI and ddG.

  DOI：

  10.1016/s0040-4020(01)86501-7
• 作为产物：
  描述：

  methyl 5-O-benzoyl-β-D-ribofuranoside 在 sodium hydroxide 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 Benzoic acid (2S,5R)-5-methoxy-2,5-dihydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Novel dideoxynucleoside isosteres

  摘要：

  Novel 5-aza-7-deaza isosteres of the anti-HIV compounds, dideoxyinosine (ddI) and dideoxyguanosine (ddG), have been prepared by glycosylation of the corresponding isosteric bases with appropriately tailored dideoxyribose components. The glycosylation reactions were regiospecific and the position of glycosylation was established by UV and high-field NMR data. However, attempted preparation of the 3-deaza-5-aza isostere of dideoxyinosine led to a different regioisomer, a ring-extended dideoxycytidine analogue, whose structure was established by X-ray crystallographic data. The 5-aza-7-deaza isosteres of ddI and ddG were more stable with respect to hydrolytic cleavage than ddI and ddG.

  DOI：

  10.1016/s0040-4020(01)86501-7

文献信息

• 一种甲基酮衍生物及其制备方法与应用
  申请人：苏州大学

  公开号：CN106496130B

  公开（公告）日：2019-09-20

  本发明公开了一种甲基酮衍生物及其制备方法与应用，将酮衍生物、有机过氧化物溶于溶剂中，于80‑130℃反应，获得甲基嘧啶酮和甲基吡啶酮衍生物。本发明使用酮衍生物为起始物，原料易得、种类很多；利用本发明的方法得到的产物类型多样，既可以直接使用、又可以用于其他进一步的反应。本发明方法无金属参与，适合于制药工艺。本发明方法路线简短、反应条件温和、反应操作和后处理过程简单、产率较高，适合于规模化生产。
• Novel dideoxynucleoside isosteres
  作者：Vasu Nair、Arthur G. Lyons、David F. Purdy

  DOI：10.1016/s0040-4020(01)86501-7

  日期：1991.11

  Novel 5-aza-7-deaza isosteres of the anti-HIV compounds, dideoxyinosine (ddI) and dideoxyguanosine (ddG), have been prepared by glycosylation of the corresponding isosteric bases with appropriately tailored dideoxyribose components. The glycosylation reactions were regiospecific and the position of glycosylation was established by UV and high-field NMR data. However, attempted preparation of the 3-deaza-5-aza isostere of dideoxyinosine led to a different regioisomer, a ring-extended dideoxycytidine analogue, whose structure was established by X-ray crystallographic data. The 5-aza-7-deaza isosteres of ddI and ddG were more stable with respect to hydrolytic cleavage than ddI and ddG.