2,5-anhdyro-4-deoxy-4-(thymin-1-yl)-L-mannofuranose dimethyl acetal | 196596-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhdyro-4-deoxy-4-(thymin-1-yl)-L-mannofuranose dimethyl acetal
• 英文别名: 2,5-Anhydro-4-deoxy-4-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1-(dimethyl acetal)-L-mannose；1-[(2R,3R,4R,5R)-5-(dimethoxymethyl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-5-methylpyrimidine-2,4-dione
• CAS: 196596-85-7
• 化学式: C₁₃H₂₀N₂O₇
• 分子量: 316.311
• InChiKey: LQORNWXDTZHUCA-AXTSPUMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-anhdyro-4-deoxy-4-(thymin-1-yl)-L-mannofuranose dimethyl acetal 在 sodium azide 、 四溴化碳 、 4-甲苯硫酚 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 1-((2S,3R,4R,5R)-2-Aminomethyl-5-dimethoxymethyl-4-hydroxy-tetrahydro-furan-3-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  One-step synthesis of novel tricyclic isomeric azidonucleosides

  摘要：

  Several tricyclic azido-isonucleosides were formed in high yields by the treatment of pyrimidine isonucleosides with triphenylphosphine, tetrabromomethane, and sodium azide. The regioselective ring opening of these tricyclic azido-isonucleosides was also investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.034
• 作为产物：
  描述：

  3-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal 在 甲醇 、 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 2,5-anhdyro-4-deoxy-4-(thymin-1-yl)-L-mannofuranose dimethyl acetal
  参考文献：
  名称：

  Stereoselective synthesis of 4-deoxy-4-nucleobase-2,5-anhydro-l-mannitol derivatives

  摘要：

  2,5:3,4-Dianhydro-L-talofuranose dimethylacetal 7 was synthesized from D-glucose in 7 steps. A series of 4-deoxy-4-nucleobase-2,5-anhydro-L-mannitols 13-16 were synthesized regioselectively from 7 in good yields. 6-O-p-Tolylsulfonyl-2,5:3,4-dianhydro-L-talofuranose dimethylacetal 8 reacted with uracil or thymine to give the corresponding isonucleosides 17 and 19, but in the case of reaction of 8 with adenine, reformation of tetrahydrofuran ring took place, giving 4-(S)-adenyl-5-(R)-[1'-(R)-hydroxy-2',2'-dimethoxyl] ethyl-2,3-dihydrofuran 21 and 4-deoxy-4-adenyl-2,5:3,6-dianhydro-L-mannofuranose dimethylacetal 22. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00314-5

文献信息

• Synthesis and Duplex Stabilization of Oligonucleotides Consisting of Isonucleosides
  作者：Zhenjun Yang、Huyi Zhang、Jimei Min、Lingtai Ma、Lihe Zhang

  DOI：10.1002/(sici)1522-2675(19991110)82:11<2037::aid-hlca2037>3.0.co;2-i

  日期：1999.11.10

  Novel oligonucleotide analogues built from isonucleosides were synthesized by the phosphoramidite approach on an automated DNA synthesizer. The phosphoramidite building blocks were synthesized by phosphitylation of the corresponding protected isonucleosides. The oligonucleotide analogues C - G containing the isonucleoside 1-3 were studied with respect to their hybridization properties and enzymatic stability. The oligomers bearing an isonucleoside at the end of the strands all proved stable towards snake-venom phosphodiesterase, but only the oligomers D-G exhibit acceptable duplex stability when hybridized with complementary d(A(14)).
• Studies on Modified Oligonucleotides
  作者：Li He Zhang、Zhen Jun Yang、Liang Ren Zhang

  DOI：10.1080/10426500701734539

  日期：2008.1.14
• Stereoselective synthesis of 4-deoxy-4-nucleobase-2,5-anhydro-l-mannitol derivatives
  作者：Z.J. Yang、H.W. Yu、J.M. Min、L.T. Ma、L.H. Zhang

  DOI：10.1016/s0957-4166(97)00314-5

  日期：1997.8

  2,5:3,4-Dianhydro-L-talofuranose dimethylacetal 7 was synthesized from D-glucose in 7 steps. A series of 4-deoxy-4-nucleobase-2,5-anhydro-L-mannitols 13-16 were synthesized regioselectively from 7 in good yields. 6-O-p-Tolylsulfonyl-2,5:3,4-dianhydro-L-talofuranose dimethylacetal 8 reacted with uracil or thymine to give the corresponding isonucleosides 17 and 19, but in the case of reaction of 8 with adenine, reformation of tetrahydrofuran ring took place, giving 4-(S)-adenyl-5-(R)-[1'-(R)-hydroxy-2',2'-dimethoxyl] ethyl-2,3-dihydrofuran 21 and 4-deoxy-4-adenyl-2,5:3,6-dianhydro-L-mannofuranose dimethylacetal 22. (C) 1997 Elsevier Science Ltd.
• One-step synthesis of novel tricyclic isomeric azidonucleosides
  作者：Zong-Sheng Li、Ren-Ping Qiao、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.tetasy.2006.03.034

  日期：2006.4

  Several tricyclic azido-isonucleosides were formed in high yields by the treatment of pyrimidine isonucleosides with triphenylphosphine, tetrabromomethane, and sodium azide. The regioselective ring opening of these tricyclic azido-isonucleosides was also investigated. (c) 2006 Elsevier Ltd. All rights reserved.