methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside | 188349-19-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
• CAS: 188349-19-1
• 化学式: C₁₆H₁₇BrF₃NO₅
• 分子量: 440.214
• InChiKey: WVXNTBLDCFSJCH-RVMXOQNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以95%的产率得到methyl 4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  Synthesis of 6-Hydroxy-L-Daunosamine and L-Daunosamine Derivatives

  摘要：

  Methyl 3-trifluoroacetamido-2,3-dideoxy-alpha-L-lyxo-hexopyranoside (19) has been synthesized from D-glucose derivatives following two pathways. The first one involving 1,2:5,6-di-O-isopropylidene-alpha-D-glucopyranose as starting material is mainly based upon azidation at C-3, inversion of configuration at C-5 and then radical deoxygenation at C-2 (13 steps and 10% overall yield). This pathway also afforded methyl N-trifluoroacetyl-alpha-L-daunosamine 22. The second pathway, which started from tri-O-acetyl-D-glucal, relied essentially upon Michael addition of N3H on the corresponding hex-2-enose and glycosidation of the two pivaloyl compounds 33 and 34. After the beta-D-ribo isomer 34 was subsequently converted into its beta-methyl glycoside 28b, inversion of configuration at C-5 was carried out via the formation of the 6-bromo-sugar 36, followed by formation of the hex-5-enopyranoside 37. Hydroboration of 37 stereoselectively afforded 38, followed by catalytic hydrogenation and trifluoroacetylation to give 19.

  DOI：

  10.1080/07328309708006508
• 作为产物：
  描述：

  在 palladium on activated charcoal 吡啶 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 、 氢气 、 三正丁基氢锡 、 sodium methylate 、 三乙胺 、 barium carbonate 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 二氯甲烷 、 三乙胺 、 甲苯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 46.3h， 生成 methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  Synthesis of 6-Hydroxy-L-Daunosamine and L-Daunosamine Derivatives

  摘要：

  Methyl 3-trifluoroacetamido-2,3-dideoxy-alpha-L-lyxo-hexopyranoside (19) has been synthesized from D-glucose derivatives following two pathways. The first one involving 1,2:5,6-di-O-isopropylidene-alpha-D-glucopyranose as starting material is mainly based upon azidation at C-3, inversion of configuration at C-5 and then radical deoxygenation at C-2 (13 steps and 10% overall yield). This pathway also afforded methyl N-trifluoroacetyl-alpha-L-daunosamine 22. The second pathway, which started from tri-O-acetyl-D-glucal, relied essentially upon Michael addition of N3H on the corresponding hex-2-enose and glycosidation of the two pivaloyl compounds 33 and 34. After the beta-D-ribo isomer 34 was subsequently converted into its beta-methyl glycoside 28b, inversion of configuration at C-5 was carried out via the formation of the 6-bromo-sugar 36, followed by formation of the hex-5-enopyranoside 37. Hydroboration of 37 stereoselectively afforded 38, followed by catalytic hydrogenation and trifluoroacetylation to give 19.

  DOI：

  10.1080/07328309708006508