1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl-α-D-allofuranose | 177361-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl-α-D-allofuranose
• 英文别名: 3-C-trifluoromethyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose；(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-(trifluoromethyl)-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 177361-82-9
• 化学式: C₁₃H₁₉F₃O₆
• 分子量: 328.285
• InChiKey: PBKQBPUPZQBOGG-LOLAFCHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl-α-D-allofuranose 在 溶剂黄146 作用下， 以 水 为溶剂， 以95 %的产率得到
  参考文献：
  名称：

  Carbohydrate-Templated Syntheses of Trifluoromethyl-Substituted MEP Analogues for the Study of the Methylerythritol Phosphate Pathway

  摘要：

  DOI：

  10.1021/acs.joc.3c01910
• 作为产物：
  描述：

  [(3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-trifluoromethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-trimethyl-silane 在 甲醇 、 四丁基氟化铵 作用下， 反应 1.0h， 生成 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl-α-D-allofuranose
  参考文献：
  名称：

  Synthesis of 3-Deoxy-3-C-Trifluoromethyl-d-Ribose Fromd-Xylose ord-Glucose

  摘要：

  The synthesis of 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-alpha-D-ribofuranose is described. After a first approach from a commercial D-xylose derivative which was limited by an incomplete stereoselectivity, the synthesis of the title compound was performed from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose by a reaction sequence where key steps: trifluoromethylation with CF(3)SiMe(3) and radical deoxygenation are highly stereoselective.

  DOI：

  10.1080/07328309608005659

文献信息

• Unprecedented 3- O -methyl-3- C -trifluoromethyl- d -ribono- (and l -lyxono)-γ-lactones synthesized by nucleophilic trifluoromethylation of d -hexose-derived cyclic ketones
  作者：Siwar Ghannay、Jihed Brahmi、Kaïss Aouadi、Moncef Msadek、Jean-Pierre Praly

  DOI：10.1016/j.jfluchem.2016.05.002

  日期：2016.6

  d-ribono-(and l-lyxono)-γ-lactones have been prepared from protected d-hexoses (gluco, galacto) by multi-step routes from d-glucose. The synthetic strategy includes the following steps: regioselective oxidation, nucleophilic trifluoromethylation with the Ruppert-Prakash reagent of 3-keto hexofuranose derivatives attacked stereoselectively from the less hindered face, protective group manipulations

  3- ø -甲基-3- Ç三氟甲基- d -ribono-（和升-lyxono）-γ-内酯已经从保护制备d -hexoses（葡萄糖，半乳糖）通过从多步途径d -葡萄糖。合成策略包括以下步骤：区域选择性氧化，3-酮基六呋喃糖衍生物的Ruppert-Prakash试剂的Ruppert-Prakash试剂进行亲核三氟甲基化，从较少受阻的面部进行立体选择性攻击，保护基操作和半缩醛羟基的区域选择性氧化。两种相关的d-核糖内酯的碱催化水解得到3 - O -Me-3- C-CF 3 - d -ribonic酸。
• WO2007/113538
  申请人：——

  公开号：——

  公开（公告）日：——
• Stereoselectivity of the nucleophilic F-alkylation of carbonylated carbohydrates
  作者：Sandrine Lavaire、Richard Plantier-Royon、Charles Portella

  DOI：10.1016/s0957-4166(97)00620-4

  日期：1998.1

  The addition of F-alkyl organometallics to carbonylated carbohydrates 1-3 was carried out using trimethylsilyl or bromomagnesium reagents. The results are strongly dependent upon both the nature of the metal and of the substrate. Compounds 1 and 2 were transformed with high stereoselectivity into the L-ido adduct using F-organomagnesium reagents, whereas the D-allo adduct was obtained with complete stereoselectivity using fluoride activated addition of F-organosilanes on compound 3. Comparison with literature data emphasizes the enhanced stereoselectivity exhibited by perfluoroorgoanometallic reagents. The difference between the stereoselectivity of the addition of magnesium versus silyl reagents was attributed to chelation effects. (C) 1998 Elsevier Science Ltd. All rights reserved.
• SUBSTITUTED ADENINES AND THE USES THEREOF
  申请人：AstraZeneca AB

  公开号：EP2010553A1

  公开（公告）日：2009-01-07
• [EN] SUBSTITUTED ADENINES AND THE USES THEREOF<br/>[FR] ADÉNINES SUBSTITUÉES ET LEUR UTILISATION
  申请人：ASTRAZENECA AB

  公开号：WO2007113538A1

  公开（公告）日：2007-10-11

  [EN] This invention relates to compounds of Formula (I) or Formula (II): their intermediates and the use of compounds of Formula (I) or Formula (II) in the treatment of bacterial infections.
  [FR] La présente invention concerne des composés répondant à la formule (I) ou à la formule (II), leurs intermédiaires et l'utilisation de composés répondant à la formule I ou à la formule II dans le traitement d'infections bactériennes.