1-(3-amino-2,3-dideoxy-β-D-arabino-hexopyranosyl)uracil | 80646-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(3-amino-2,3-dideoxy-β-D-arabino-hexopyranosyl)uracil
• 英文别名: 1-(3-amino-2,3-dideoxy-β-D-arabinohexopyranosyl)uracil；1-(3-amino-2,3-dideoxy-beta-D-glucopyranosyl)uracil；1-[(2R,4R,5S,6R)-4-amino-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]pyrimidine-2,4-dione
• CAS: 80646-96-4
• 化学式: C₁₀H₁₅N₃O₅
• 分子量: 257.246
• InChiKey: HJJUSGVWHJXMIU-GCXDCGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-(3-amino-2,3-dideoxy-β-D-arabino-hexopyranosyl)uracil 以 吡啶 为溶剂， 反应 4.5h， 以98%的产率得到1-(3-acetamido-4,6-di-O-acetyl-2,3-dideoxy-β-D-arabinohexopyranosyl)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-glucopyranosyl)uracil 在 吡啶 、 tin 、 sodium tetrahydroborate 、 水 、 乙酸酐 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 9.67h， 生成 1-(3-amino-2,3-dideoxy-β-D-arabino-hexopyranosyl)uracil
  参考文献：
  名称：

  Stereoselective Reactions OF 1-(4,6-O-Benzylidene-2,3-Didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil with some Nucleophiles¶

  摘要：

  Michael addition of benzylamine, piperidine, morpholine, pyrrolidine, cyclohexylamine, allylamine and dimethylmalonate to the nitroolefin (5) generated in situ from 1-(4,6-O-benzylidene-3-deoxy-3-nitro-beta-D-glucopyranosyl)uracil (4b) gave the corresponding 2-(substituted-amino)-3-deoxy-3-nitro-beta-D-glucopyranosides (6a-f and 6h). Reaction of 4b with N,N'-carbonyldiimidazole directly gave 6g. Compound 4b was converted into the 2-deoxy analogue (8), which was reduced to the 3-amino (9) and 3-hydroxylamino analogue (10).

  DOI：

  10.1080/07328319608002131

文献信息

• L-nucleoside analogues and pharmaceutical compositions
  申请人：Medivir AB

  公开号：US05747473A1

  公开（公告）日：1998-05-05

  ##STR1## Novel antiviral compounds of formulae (1A) and (1B), wherein X and R.sub.1 -R.sub.4 are as stated in claim 1 in the form of an .alpha.- or .beta.-anomer or a mixture thereof, and pharmaceutically acceptable salts thereof, are disclosed, as well as a new method for preparation thereof. Said compounds can be used for treatment of infections caused by viruses requiring reverse transcriptase for replication, such as HIV and hepatitis B virus.

  本发明公开了式（1A）和（1B）的新型抗病毒化合物，其中X和R.sub.1-R.sub.4如权利要求书中所述，以α-或β-异构体或其混合物的形式存在，并且其药物可接受的盐，以及其制备的新方法。所述化合物可用于治疗由需要反转录酶复制的病毒引起的感染，例如HIV和乙型肝炎病毒。
• US5473063A
  申请人：——

  公开号：US5473063A

  公开（公告）日：1995-12-05
• US5747473A
  申请人：——

  公开号：US5747473A

  公开（公告）日：1998-05-05
• US5952500A
  申请人：——

  公开号：US5952500A

  公开（公告）日：1999-09-14
• US6121431A
  申请人：——

  公开号：US6121431A

  公开（公告）日：2000-09-19