1-(4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-lyxohexopyranosyl)uracil | 175471-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-(4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-lyxohexopyranosyl)uracil
• 英文别名: 1-[(4aR,6R,8R,8aR)-8-nitro-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]pyrimidine-2,4-dione
• CAS: 175471-10-0
• 化学式: C₁₇H₁₇N₃O₇
• 分子量: 375.338
• InChiKey: IMYZHPPOEVEWQI-KGFCIHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  125.69
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-lyxohexopyranosyl)uracil 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 乙酸酐 、 三氟乙酸 作用下， 反应 3.83h， 生成 1-(2,3,4-trideoxy-3-nitro-β-D-threohexopyranosyl)uracil
  参考文献：
  名称：

  Polydeoxyaminohexopyranosylnucleosides. Synthesis of 1-(2,3,4-Trideoxy-3-nitro-β-D-erythro- andthreo-hexopyranosyl)-uracils from Uridine

  摘要：

  The first synthesis of nitro-multideoxy-sugar containing nucleosides was achieved. 1-(4,6-O-Benzyiidene-3-deoxy-3-nitro-beta-D-glucopyranosyl)uracil (3) was converted in 75% yield into 1-(4,6-O-benzylidene-2,3-dideoxy-3-nitro-arabinohexopyranosyl)uracil (7) by acetylation followed by NaBH4 reduction in methanol. De-O-benzylidenation with CF3CO2H afforded crystalline 1-(2,3-dideoxy-3-nitro-beta-D-arabinohexopyranosyl)uracil (8) was obtained in 87% yield. Raney Ni reduction of 8 afforded the corresponding 3'-amino-nucleoside 9. Acetylation of 8 followed by NaBH4 treatment afforded an 8.1 mixture from which 1-(2,3,4-trideoxy-3-nitro-beta-D-threohexopyranosyl)-uracil (14) was obtained in pure crystalline form. After Raney Ni reduction of the mixture, 1-(3-amino-2,3,4-trideoxy-beta-D-threohexopyranosyl)uracil (16) and its erythro epimer 21 were isolated. 1-(4,6-O-Benzylidene-2, 3 dideoxy-3-nitro-beta-D-lyxohexopyranosyl)uracil (24) was prepared in 72% yield from 1-(4,6-O-benzylidene-3 -deoxy-3-nitro-beta-D-galactopyranosyl)uracil (4) by acetylation and subsequent reduction with NaBH4. De-O-benzylid-enation of 23 afforded 1-(2,3,4-trideoxy-3-nitro-beta-D-lyxohexopyranosyl)uracil (25) in 83% yield. Schmidt-Rutz reaction of 25 followed by NaBH4 reduction afforded a mixture of three and erythro isomers of 2',3',4'-trideoxy-3'-nitrohexopyranosyluracil, from which pure 16 and 21 were obtained.

  DOI：

  10.1080/07328319608002380
• 作为产物：
  描述：

  1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-galactopyranosyl)uracil 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 乙酸酐 作用下， 生成 1-(4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-lyxohexopyranosyl)uracil
  参考文献：
  名称：

  Polydeoxyaminohexopyranosylnucleosides. Synthesis of 1-(2,3,4-Trideoxy-3-nitro-β-D-erythro- andthreo-hexopyranosyl)-uracils from Uridine

  摘要：

  The first synthesis of nitro-multideoxy-sugar containing nucleosides was achieved. 1-(4,6-O-Benzyiidene-3-deoxy-3-nitro-beta-D-glucopyranosyl)uracil (3) was converted in 75% yield into 1-(4,6-O-benzylidene-2,3-dideoxy-3-nitro-arabinohexopyranosyl)uracil (7) by acetylation followed by NaBH4 reduction in methanol. De-O-benzylidenation with CF3CO2H afforded crystalline 1-(2,3-dideoxy-3-nitro-beta-D-arabinohexopyranosyl)uracil (8) was obtained in 87% yield. Raney Ni reduction of 8 afforded the corresponding 3'-amino-nucleoside 9. Acetylation of 8 followed by NaBH4 treatment afforded an 8.1 mixture from which 1-(2,3,4-trideoxy-3-nitro-beta-D-threohexopyranosyl)-uracil (14) was obtained in pure crystalline form. After Raney Ni reduction of the mixture, 1-(3-amino-2,3,4-trideoxy-beta-D-threohexopyranosyl)uracil (16) and its erythro epimer 21 were isolated. 1-(4,6-O-Benzylidene-2, 3 dideoxy-3-nitro-beta-D-lyxohexopyranosyl)uracil (24) was prepared in 72% yield from 1-(4,6-O-benzylidene-3 -deoxy-3-nitro-beta-D-galactopyranosyl)uracil (4) by acetylation and subsequent reduction with NaBH4. De-O-benzylid-enation of 23 afforded 1-(2,3,4-trideoxy-3-nitro-beta-D-lyxohexopyranosyl)uracil (25) in 83% yield. Schmidt-Rutz reaction of 25 followed by NaBH4 reduction afforded a mixture of three and erythro isomers of 2',3',4'-trideoxy-3'-nitrohexopyranosyluracil, from which pure 16 and 21 were obtained.

  DOI：

  10.1080/07328319608002380