methyl 3-azido-2,3-dideoxy-α-L-lyxo-hexopyranoside | 188349-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-2,3-dideoxy-α-L-lyxo-hexopyranoside
• 英文别名: (2S,3S,4S,6R)-4-azido-2-(hydroxymethyl)-6-methoxyoxan-3-ol
• CAS: 188349-28-2
• 化学式: C₇H₁₃N₃O₄
• 分子量: 203.198
• InChiKey: FLZWXHAJKPSXOG-YTLHQDLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-2,3-dideoxy-α-L-lyxo-hexopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (2S,3S,4S,6R)-4-Amino-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ol
  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：

  ((2R,3S)-3-acetoxy-6-hydroxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate 在 吡啶 、 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 K₁₀ montmorillonite 、 sodium methylate 、 silver fluoride 、 对甲苯磺酸 、 溶剂黄146 、 9-硼双环[3.3.1]壬烷 、 barium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 60.0 ℃ 、2.67 kPa 条件下， 反应 104.5h， 生成 methyl 3-azido-2,3-dideoxy-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