3-O-benzyl-6-deoxy-6,6,6-trifluoro-1,2-O-isopropylidene-α-D-glucofuranose | 138430-42-9

• 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: 3-O-benzyl-6-deoxy-6,6,6-trifluoro-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: (1S)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2,2,2-trifluoroethanol
• CAS: 138430-42-9
• 化学式: C₁₆H₁₉F₃O₅
• 分子量: 348.319
• InChiKey: QGJIGXAQSXPIDY-PDWCTOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (三氟甲基)三甲基硅烷 、 3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 在 四丁基醋酸铵 、 四丁基氟化铵 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 3-O-benzyl-6-deoxy-6,6,6-trifluoro-1,2-O-isopropylidene-α-D-glucofuranose 、 3-O-benzyl-6-deoxy-6,6,6-trifluoro-1,2-O-isopropylidene-β-L-idofuranose
  参考文献：
  名称：

  路易斯碱催化羰基化合物和亚胺与（全氟烷基）三甲基硅烷的全氟烷基化

  摘要：

  描述了路易斯碱催化羰基化合物和醛亚胺与（全氟烷基）三甲基硅烷（TMSCF3、TMSC2F5 和 TMSC3F7）的全氟烷基化。含氮或含氧...

  DOI：

  10.1246/bcsj.79.1133

文献信息

• Trifluoromethylation of chiral aldehyde and synthesis of 6-deoxy-6,6,6-trifluorohexoses.
  作者：Yuji HANZAWA、Jun-ichiro UDA、Yoshiro KOBAYASHI、Yoshiharu ISHIDO、Takeo TAGUCHI、Motoo SHIRO

  DOI：10.1248/cpb.39.2459

  日期：——

  Trifluoromethylation of chiral aldehyde derived from suger was efficiently carried out by a modification of the reported procedure. The preparation of 6, 6, 6-trifluoro-L-daunosamine was also achieved by using (2S, 3R)-4, 4, 4-trifluorobutane-1, 2, 3-triol derivative.

  通过对已报道程序的改进，高效地实现了源自糖醛的手性醛的三氟甲基化。使用 (2S, 3R)-4, 4, 4-三氟丁烷-1, 2, 3-三醇衍生物还制备了 6, 6, 6-三氟-L-杜诺萨明。
• 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.
• Lewis Base-Catalyzed Perfluoroalkylation of Carbonyl Compounds and Imines with (Perfluoroalkyl)trimethylsilane
  作者：Yoshikazu Kawano、Nobuya Kaneko、Teruaki Mukaiyama

  DOI：10.1246/bcsj.79.1133

  日期：2006.7

  Lewis base-catalyzed perfluoroalkylation of carbonyl compounds and aldimines with (perfluoroalkyl)trimethylsilanes (TMSCF3, TMSC2F5, and TMSC3F7) is described. The nitrogen- or oxygen-containing an...

  描述了路易斯碱催化羰基化合物和醛亚胺与（全氟烷基）三甲基硅烷（TMSCF3、TMSC2F5 和 TMSC3F7）的全氟烷基化。含氮或含氧...